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Volumn 67, Issue 1, 2013, Pages 84-91

Total synthesis of N,O,O,O-tetraacetyl-d-ribo-phytosphingosine and its 2-epi-congener

Author keywords

aza Claisen rearrangement; isothiocyanates; microwave irradiation; phytosphingosine

Indexed keywords


EID: 84866757687     PISSN: 03666352     EISSN: 13369075     Source Type: Journal    
DOI: 10.2478/s11696-012-0245-0     Document Type: Article
Times cited : (14)

References (42)
  • 3
    • 0034596034 scopus 로고    scopus 로고
    • Stereospecific total synthesis of sphingosine and its analogues from L-serine
    • 10.1021/jo991447x 1:CAS:528:DC%2BD3cXivVGqtLo%3D
    • Azuma, H., Tamagaki, S., & Ogino, K. (2000). Stereospecific total synthesis of sphingosine and its analogues from L-serine. The Journal of Organic Chemistry, 65, 3538-3541. DOI: 10.1021/jo991447x.
    • (2000) The Journal of Organic Chemistry , vol.65 , pp. 3538-3541
    • Azuma, H.1    Tamagaki, S.2    Ogino, K.3
  • 4
    • 70349758237 scopus 로고    scopus 로고
    • Efficient synthesis of d-xylo and d-ribo-phytosphingosines from methyl 2-amino-2-deoxy-β-d-hexopyranosides
    • 10.1016/j.carres.2009.07.007 1:CAS:528:DC%2BD1MXht1Ggt7zM
    • Cai, Y., Ling, C. C., & Bundle, D. R. (2009). Efficient synthesis of d-xylo and d-ribo-phytosphingosines from methyl 2-amino-2-deoxy-β-d- hexopyranosides. Carbohydrate Research, 344, 2120-2126. DOI: 10.1016/j.carres.2009.07.007.
    • (2009) Carbohydrate Research , vol.344 , pp. 2120-2126
    • Cai, Y.1    Ling, C.C.2    Bundle, D.R.3
  • 5
    • 34047261471 scopus 로고    scopus 로고
    • Synthesis of phytosphingosine using olefin cross-metathesis: A convenient access to chain modified phytosphingosines from d-lyxose
    • 10.1016/j.tet.2007.03.047 1:CAS:528:DC%2BD2sXktF2hs7c%3D
    • Chang, C. W., Chen, Y. N., Adak, A. K., Lin, K. H., Tzou, D. L. M., & Lin, C. C. (2007). Synthesis of phytosphingosine using olefin cross-metathesis: a convenient access to chain modified phytosphingosines from d-lyxose. Tetrahedron, 63, 4310-4318. DOI: 10.1016/j.tet.2007.03.047.
    • (2007) Tetrahedron , vol.63 , pp. 4310-4318
    • Chang, C.W.1    Chen, Y.N.2    Adak, A.K.3    Lin, K.H.4    Tzou, D.L.M.5    Lin, C.C.6
  • 6
    • 0034625349 scopus 로고    scopus 로고
    • Sphingolipids signal heat stress-induced ubiquitin-dependent proteolysis
    • 10.1074/jbc.C000229200 1:CAS:528:DC%2BD3cXktFalu7s%3D
    • Chung, N., Jenkins, G., Hannun, Y. A., Heitman, J., & Obeid, L. M. (2000). Sphingolipids signal heat stress-induced ubiquitin-dependent proteolysis. The Journal of Biological Chemistry, 275, 17229-17232. DOI: 10.1074/jbc.c000229200.
    • (2000) The Journal of Biological Chemistry , vol.275 , pp. 17229-17232
    • Chung, N.1    Jenkins, G.2    Hannun, Y.A.3    Heitman, J.4    Obeid, L.M.5
  • 7
    • 65549085778 scopus 로고    scopus 로고
    • 18-phytosphingosine
    • 10.1016/j.tetlet.2009.02.173 1:CAS:528:DC%2BD1MXmtVemsb4%3D
    • 18-phytosphingosine. Tetrahedron Letters, 50, 3425-3427. DOI: 10.1016/j.tetlet.2009.02.173.
    • (2009) Tetrahedron Letters , vol.50 , pp. 3425-3427
    • Dubey, A.1    Kumar, P.2
  • 8
    • 79952489906 scopus 로고    scopus 로고
    • A short stereoselective synthesis of the protected uracil 3′-epi-polyoxin C
    • 10.1016/j.tetasy.2011.02.004 1:CAS:528:DC%2BC3MXjtFGktb8%3D
    • Gonda, J., Martinkova, M., & Baur, A. (2011). A short stereoselective synthesis of the protected uracil 3′-epi-polyoxin C. Tetrahedron: Asymmetry, 22, 207-214. DOI: 10.1016/j.tetasy.2011.02.004.
    • (2011) Tetrahedron: Asymmetry , vol.22 , pp. 207-214
    • Gonda, J.1    Martinkova, M.2    Baur, A.3
  • 9
    • 0028788313 scopus 로고
    • Substrate acidities and conversion times for reactions of amides with di-tert-butyl dicarbonate
    • 10.1016/0040-4039(95)01931-7 1:CAS:528:DyaK2MXpslyjsL8%3D
    • Hansen, M. M., Harkness, A. R., & Coffey, D. S. (1995). Substrate acidities and conversion times for reactions of amides with di-tert-butyl dicarbonate. Tetrahedron Letters, 36, 8949-8952. DOI: 10.1016/0040-4039(95) 01931-7.
    • (1995) Tetrahedron Letters , vol.36 , pp. 8949-8952
    • Hansen, M.M.1    Harkness, A.R.2    Coffey, D.S.3
  • 10
    • 0034602357 scopus 로고    scopus 로고
    • A stereocontrolled, efficient synthetic route to bioactive sphingolipids: Synthesis of phytosphingosine and phytoceramides from unsaturated ester precursors via cyclic sulfate intermediates
    • 10.1021/jo001225v 1:CAS:528:DC%2BD3cXntVens74%3D
    • He, L., Byun, H. S., & Bittman, R. (2000). A stereocontrolled, efficient synthetic route to bioactive sphingolipids: Synthesis of phytosphingosine and phytoceramides from unsaturated ester precursors via cyclic sulfate intermediates. The Journal Organic Chemistry, 65, 7618-7626. DOI: 10.1021/jo001225v.
    • (2000) The Journal Organic Chemistry , vol.65 , pp. 7618-7626
    • He, L.1    Byun, H.S.2    Bittman, R.3
  • 11
    • 0003023759 scopus 로고    scopus 로고
    • Occurence and significance
    • B. Fraser-Reid K. Tatsuta J. Thiem (eds) 1st ed. Springer New York, NY, USA 10.1007/978-3-642-56874-9-49
    • Holst, O. (2001). Occurence and significance. In B. Fraser-Reid, K. Tatsuta, & J. Thiem (Eds.), Glycoscience: Chemistry and chemical biology (1st ed., pp. 2083-2106). New York, NY, USA: Springer.
    • (2001) Glycoscience: Chemistry and Chemical Biology , pp. 2083-2106
    • Holst, O.1
  • 12
    • 0036231270 scopus 로고    scopus 로고
    • The preparation and biological significance of phytosphingosines
    • 10.2174/1385272024604998 1:CAS:528:DC%2BD38Xmslyiu74%3D
    • Howell, A. R., & Ndakala, A. J. (2002). The preparation and biological significance of phytosphingosines. Current Organic Chemistry, 6, 365-391. DOI: 10.2174/1385272024604998.
    • (2002) Current Organic Chemistry , vol.6 , pp. 365-391
    • Howell, A.R.1    Ndakala, A.J.2
  • 13
    • 0032480389 scopus 로고    scopus 로고
    • A short and efficient synthesis of phytosphingosines using asymmetric dihydroxylation
    • 10.1016/S0040-4020(98)00615-2 1:CAS:528:DyaK1cXls1Gjsrc%3D
    • Imashiro, R., Sakurai, O., Yamishita, T., & Horikawa, H. (1998). A short and efficient synthesis of phytosphingosines using asymmetric dihydroxylation. Tetrahedron, 54, 10657-10670. DOI: 10.1016/s0040-4020(98)00615- 2.
    • (1998) Tetrahedron , vol.54 , pp. 10657-10670
    • Imashiro, R.1    Sakurai, O.2    Yamishita, T.3    Horikawa, H.4
  • 14
    • 33846213597 scopus 로고    scopus 로고
    • Highly anti-selective dihydroxylation of 1,2-dialkyl substituted (Z)-allylic amines: Stereoselective synthesis of d-ribo-phytosphingosine derivative
    • 10.1016/j.tetlet.2006.12.084 1:CAS:528:DC%2BD2sXotFWksg%3D%3D
    • Jeon, J., Shin, M., Yoo, J. W., Oh, J. S., Bae, J. G., Jung, S. H., & Kim, Y. G. (2007). Highly anti-selective dihydroxylation of 1,2-dialkyl substituted (Z)-allylic amines: stereoselective synthesis of d-ribo-phytosphingosine derivative. Tetrahedron Letters, 48, 1105-1108. DOI: 10.1016/j.tetlet.2006.12.084.
    • (2007) Tetrahedron Letters , vol.48 , pp. 1105-1108
    • Jeon, J.1    Shin, M.2    Yoo, J.W.3    Oh, J.S.4    Bae, J.G.5    Jung, S.H.6    Kim, Y.G.7
  • 15
    • 0014408193 scopus 로고
    • Studies on sphingosines, XIV. on the phytosphingosine content of the major human kidney glycolipids
    • 10.1016/0005-2760(68)90029-5 1:CAS:528:DyaF1cXls1Oitg%3D%3D
    • Karlsson, K. A., & Mårtensson, E. (1968). Studies on sphingosines, XIV. On the phytosphingosine content of the major human kidney glycolipids. Biochimica et Biophysica Acta Lipid and Lipid Metabolism, 152, 230-233. DOI: 10.1016/0005-2760(68)90029-5.
    • (1968) Biochimica et Biophysica Acta Lipid and Lipid Metabolism , vol.152 , pp. 230-233
    • Karlsson, K.A.1    Mårtensson, E.2
  • 16
    • 39349117279 scopus 로고    scopus 로고
    • Efficient and stereoselective synthesis of d-arabino-, d-lyxo-, and d-xylo-phytosphingosine from d-ribo-phytosphingosine
    • 10.1021/jo702147y 1:CAS:528:DC%2BD1cXmtFOnug%3D%3D
    • Kim, S., Lee, N., Lee, S., Lee, T., & Lee, Y. M. (2008). Efficient and stereoselective synthesis of d-arabino-, d-lyxo-, and d-xylo- phytosphingosine from d-ribo-phytosphingosine. The Journal of Organic Chemistry, 73, 1379-1385. DOI: 10.1021/jo702147y.
    • (2008) The Journal of Organic Chemistry , vol.73 , pp. 1379-1385
    • Kim, S.1    Lee, N.2    Lee, S.3    Lee, T.4    Lee, Y.M.5
  • 17
    • 33748919382 scopus 로고
    • Synthesis of 2-isothiocyanatotetrahydropyran and its reactions with amines and alcohols
    • Kniežo, L., Bernát, J., & Martinková, M. (1994). Synthesis of 2-isothiocyanatotetrahydropyran and its reactions with amines and alcohols. Chemical Papers, 48, 103-107.
    • (1994) Chemical Papers , vol.48 , pp. 103-107
    • Kniežo, L.1    Bernát, J.2    Martinková, M.3
  • 18
    • 0033152727 scopus 로고    scopus 로고
    • Sphingolipidstheir metabolic pathways and the pathobiochemistry of neurodegenerative diseases
    • 10.1002/(SICI)1521-3773(19990601)38:11<1532: AID-ANIE1532>3.0.CO;2- U 1:CAS:528:DyaK1MXjvVarsb4%3D
    • Kolter, T., & Sandhoff, K. (1999). Sphingolipidstheir metabolic pathways and the pathobiochemistry of neurodegenerative diseases. Angewandte Chemie, International Edition in English, 38, 1532-1568. DOI: 10.1002/(SICI)1521-3773(19990601)38:111532::AID-ANIE1532〉3.0.CO;2-U.
    • (1999) Angewandte Chemie, International Edition in English , vol.38 , pp. 1532-1568
    • Kolter, T.1    Sandhoff, K.2
  • 19
    • 34548533110 scopus 로고    scopus 로고
    • L-Proline catalyzed direct diastereosective aldol reactions: Towards the synthesis of lyxo-(2S,3S,4S)-phytosphingosine
    • 10.1016/j.tetasy.2007.08.018 1:CAS:528:DC%2BD2sXhtVGitrbF
    • Kumar, I., & Rode, C. V. (2007). L-Proline catalyzed direct diastereosective aldol reactions: towards the synthesis of lyxo-(2S,3S,4S)- phytosphingosine. Tetrahedron: Asymmetry, 18, 1975-1980. DOI: 10.1016/j.tetasy.2007.08.018.
    • (2007) Tetrahedron: Asymmetry , vol.18 , pp. 1975-1980
    • Kumar, I.1    Rode, C.V.2
  • 20
    • 78049324247 scopus 로고    scopus 로고
    • A general and concise asymmetric synthesis of sphingosine, safingol and phytosphingosines via tethered aminohydroxylation
    • 10.1039/c0ob00117a 1:CAS:528:DC%2BC3cXhtlentL7O
    • Kumar, P., Dubey, A., & Puranik, V. G. (2010). A general and concise asymmetric synthesis of sphingosine, safingol and phytosphingosines via tethered aminohydroxylation. Organic & Biomolecular Chemistry, 8, 5074-5086. DOI: 10.1039/c0ob00117a.
    • (2010) Organic & Biomolecular Chemistry , vol.8 , pp. 5074-5086
    • Kumar, P.1    Dubey, A.2    Puranik, V.G.3
  • 21
    • 77954110478 scopus 로고    scopus 로고
    • Asymmetric synthesis of d-ribo-phytosphingosine from 1-tetradecyne and (4-methoxyphenoxy)acetaldehyde
    • 10.1021/jo100707d 1:CAS:528:DC%2BC3cXntVCnsrc%3D
    • Liu, Z., Byun, H. S., & Bittman, R. (2010). Asymmetric synthesis of d-ribo-phytosphingosine from 1-tetradecyne and (4-methoxyphenoxy)acetaldehyde. The Journal of Organic Chemistry, 75, 4356-4364. DOI: 10.1021/jo100707d.
    • (2010) The Journal of Organic Chemistry , vol.75 , pp. 4356-4364
    • Liu, Z.1    Byun, H.S.2    Bittman, R.3
  • 22
    • 59649089627 scopus 로고    scopus 로고
    • An efficient and general enantioselective synthesis of sphingosine, phytosphingosine, and 4-substituted derivatives
    • 10.1021/ol802379b 1:CAS:528:DC%2BD1cXhsVKmtL%2FL
    • Llaveria, J., Díaz, Y., Matheu, M. I., & Castillón, S. (2009). An efficient and general enantioselective synthesis of sphingosine, phytosphingosine, and 4-substituted derivatives. Organic Letters, 11, 205-208. DOI: 10.1021/ol802379b.
    • (2009) Organic Letters , vol.11 , pp. 205-208
    • Llaveria, J.1    Díaz, Y.2    Matheu, M.I.3    Castillón, S.4
  • 23
    • 33746876672 scopus 로고    scopus 로고
    • An efficient high-yield synthesis of d-ribo-phytosphingosine
    • 10.1021/ol0612096 1:CAS:528:DC%2BD28XmtVSiu7Y%3D
    • Lombardo, M., Capdevila, M. G., Pasi, F., & Trombini, C. (2006). An efficient high-yield synthesis of d-ribo-phytosphingosine. Organic Letters, 8, 3303-3305. DOI: 10.1021/ol0612096.
    • (2006) Organic Letters , vol.8 , pp. 3303-3305
    • Lombardo, M.1    Capdevila, M.G.2    Pasi, F.3    Trombini, C.4
  • 24
    • 3543011977 scopus 로고    scopus 로고
    • Synthesis of l-lyxo-phytosphingosine and its 1-phosphonate analogue using threitol acetal synthon
    • 10.1021/jo0493065 1:CAS:528:DC%2BD2cXlsF2murs%3D
    • Lu, X., Byun, H. S., & Bittman, R. (2004). Synthesis of l-lyxo-phytosphingosine and its 1-phosphonate analogue using threitol acetal synthon. The Journal of Organic Chemistry, 69, 5433-5438. DOI: 10.1021/jo0493065.
    • (2004) The Journal of Organic Chemistry , vol.69 , pp. 5433-5438
    • Lu, X.1    Byun, H.S.2    Bittman, R.3
  • 25
    • 17044365722 scopus 로고    scopus 로고
    • An efficient synthesis of d-ribo- and l-lyxo-phytosphingosine from d-tartaric acid
    • 10.1016/j.tetlet.2005.03.063 1:CAS:528:DC%2BD2MXjtFKmsrc%3D
    • Lu, X., & Bittman, R. (2005). An efficient synthesis of d-ribo- and l-lyxo-phytosphingosine from d-tartaric acid. Tetrahedron Letters, 46, 3165-3168. DOI: 10.1016/j.tetlet.2005.03.063.
    • (2005) Tetrahedron Letters , vol.46 , pp. 3165-3168
    • Lu, X.1    Bittman, R.2
  • 26
    • 0036644101 scopus 로고    scopus 로고
    • 18-phytosphingosine from Dglucosamine via the d-allosamine derivative as key intermediates
    • 10.1016/S0040-4039(02)00919-X 1:CAS:528:DC%2BD38XksFKlt7c%3D
    • 18-phytosphingosine from Dglucosamine via the d-allosamine derivative as key intermediates. Tetrahedron Letters, 43, 4889-4892. DOI: 10.1016/s0040-4039(02)00919-x.
    • (2002) Tetrahedron Letters , vol.43 , pp. 4889-4892
    • Luo, S.Y.1    Thopate, S.R.2    Hsu, C.Y.3    Hung, S.C.4
  • 27
    • 78049296500 scopus 로고    scopus 로고
    • Total synthesis of a protected form of sphingofungin e using the [3,3]-sigmatropic rearangement of an allylic thiocyanate as the key reaction
    • 10.1016/j.carres.2010.09.016
    • Martinková, M., Gonda, J., Špakova Raschmanová, J., Slaninková, M., & Kuchár, J. (2010). Total synthesis of a protected form of sphingofungin E using the [3,3]-sigmatropic rearangement of an allylic thiocyanate as the key reaction. Carbohydrate Research, 345, 2427-2437. DOI: 10.1016/j.carres.2010.09.016.
    • (2010) Carbohydrate Research , vol.345 , pp. 2427-2437
    • Martinková, M.1    Gonda, J.2    Špakova Raschmanová, J.3    Slaninková, M.4    Kuchár, J.5
  • 29
    • 78649944149 scopus 로고    scopus 로고
    • Recent advances in the synthesis of sphingosine and phytosphingosine, molecules of biological significance
    • 10.2174/138527210793358286 1:CAS:528:DC%2BC3cXhsFygsbnI
    • Morales-Serna, J. A., Llaveria, J., Díaz, Y., Matheu, M. I., & Castillón, S. (2010). Recent advances in the synthesis of sphingosine and phytosphingosine, molecules of biological significance. Current Organic Chemistry, 14, 2483-2521. DOI: 10.2174/138527210793358286.
    • (2010) Current Organic Chemistry , vol.14 , pp. 2483-2521
    • Morales-Serna, J.A.1    Llaveria, J.2    Díaz, Y.3    Matheu, M.I.4    Castillón, S.5
  • 30
    • 0028986518 scopus 로고
    • Antitumor activities of α-, β-monogalactosylceramides and four diastereoisomers of an α-galactosylceramide
    • 10.1016/0960-894X(95)00098-E 1:CAS:528:DyaK2MXltF2gsL4%3D
    • Motoki, K., Kobayashi, E., Uchida, T., Fukushima, H., & Koezuka, Y. (1995). Antitumor activities of α-, β-monogalactosylceramides and four diastereoisomers of an α-galactosylceramide. Bioorganic & Medicinal Chemistry Letters, 5, 705-710. DOI: 10.1016/0960-894x(95)00098-e.
    • (1995) Bioorganic & Medicinal Chemistry Letters , vol.5 , pp. 705-710
    • Motoki, K.1    Kobayashi, E.2    Uchida, T.3    Fukushima, H.4    Koezuka, Y.5
  • 31
    • 0023026183 scopus 로고
    • 18-phytosphingosine from (R)-2,3-0-isopropylidene glyceraldehyde
    • 10.1016/S0040-4020(01)96078-8 1:CAS:528:DyaL1cXitFGqtw%3D%3D
    • 18-phytosphingosine from (R)-2,3-0- isopropylidene glyceraldehyde. Tetrahedron, 42, 5961-5968. DOI: 10.1016/s0040-4020(01)96078-8.
    • (1986) Tetrahedron , vol.42 , pp. 5961-5968
    • Mulzer, J.1    Brand, C.2
  • 32
    • 0037467871 scopus 로고    scopus 로고
    • 18- phytosphingosine using double stereodifferentiation
    • 10.1016/S0040-4039(02)02732-6 1:CAS:528:DC%2BD3sXhtFCnurs%3D
    • 18-phytosphingosine using double stereodifferentiation. Tetrahedron Letters, 44, 1035-1037. DOI: 10.1016/s0040-4039(02)02732-6.
    • (2003) Tetrahedron Letters , vol.44 , pp. 1035-1037
    • Naidu, S.V.1    Kumar, P.2
  • 33
    • 55549093106 scopus 로고    scopus 로고
    • Improved synthesis of phytosphingosine and dihydrosphingosine from 3,4,6-tri-O-acetyl-d-galactal
    • 10.1002/hlca.200890076 1:CAS:528:DC%2BD1cXmtVWgs7o%3D
    • Niu, Y., Cao, X., & Ye, X. S. (2008). Improved synthesis of phytosphingosine and dihydrosphingosine from 3,4,6-tri-O-acetyl-d-galactal. Helvetica Chimica Acta, 91, 746-752. DOI: 10.1002/hlca.200890076.
    • (2008) Helvetica Chimica Acta , vol.91 , pp. 746-752
    • Niu, Y.1    Cao, X.2    Ye, X.S.3
  • 34
    • 65549095945 scopus 로고    scopus 로고
    • Enantioselective total synthesis of (2S,3R,4R)-d-xylo-phytosphingosine from substituted azetidin-2-one
    • 10.1016/j.tetlet.2009.02.050 1:CAS:528:DC%2BD1MXmtVenu7o%3D
    • Pandey, G., & Tiwari, D. K. (2009). Enantioselective total synthesis of (2S,3R,4R)-d-xylo-phytosphingosine from substituted azetidin-2-one. Tetrahedron Letters, 50, 3296-3298. DOI: 10.1016/j.tetlet.2009.02.050.
    • (2009) Tetrahedron Letters , vol.50 , pp. 3296-3298
    • Pandey, G.1    Tiwari, D.K.2
  • 35
    • 80054864374 scopus 로고    scopus 로고
    • 18-phytosphingosine from d-fructose
    • 10.1016/j.tet.2011.10.003 1:CAS:528:DC%2BC3MXhtl2ht7fF
    • 18-phytosphingosine from d-fructose. Tetrahedron, 67, 9283-9290. DOI: 10.1016/j.tet.2011.10.003.
    • (2011) Tetrahedron , vol.67 , pp. 9283-9290
    • Perali, R.S.1    Mandava, S.2    Chalapala, S.3
  • 36
    • 0038645397 scopus 로고    scopus 로고
    • Novel, efficient and stereospecific synthesis of xylo-(2R,3S,4S)- phytosphingosine and threo-(2R,3R)-sphingosine
    • 10.1016/S0957-4166(03)00427-0
    • Raghvan, S., Rajender, A., & Yadav, J. S. (2003). Novel, efficient and stereospecific synthesis of xylo-(2R,3S,4S)-phytosphingosine and threo-(2R,3R)-sphingosine. Tetrahedron: Asymmetry, 14, 2093-2099. DOI: 10.1016/s0957-4166 (03)00427-0.
    • (2003) Tetrahedron: Asymmetry , vol.14 , pp. 2093-2099
    • Raghvan, S.1    Rajender, A.2    Yadav, J.S.3
  • 37
    • 84860390081 scopus 로고    scopus 로고
    • A common and stereoselective strategy for the synthesis of N,O,O,O-tetra-acetyl d-ribo-(2S,3S,4R)-phytosphingosine and 2-epi-jaspine B
    • 10.1016/j.tetlet.2010.12.039
    • Rao, G. S., & Rao, B. V. (2011a). A common and stereoselective strategy for the synthesis of N,O,O,O-tetra-acetyl d-ribo-(2S,3S,4R)- phytosphingosine and 2-epi-jaspine B. Tetrahedron Letters, 52, 4861-4864. DOI: 10.1016/j.tetlet.2011.07.032.
    • (2011) Tetrahedron Letters , vol.52 , pp. 4861-4864
    • Rao, G.S.1    Rao, B.V.2
  • 38
    • 80054104928 scopus 로고    scopus 로고
    • A common strategy for the stereoselective synthesis of anhydrophytosphingosine pachastrissamine (jaspine B) and N,O,O,O-tetra-acetyl d-lyxo-phytosphingosine
    • 10.1016/j.tetlet.2010.12.039
    • Rao, G. S., & Rao, B. V. (2011b) A common strategy for the stereoselective synthesis of anhydrophytosphingosine pachastrissamine (jaspine B) and N,O,O,O-tetra-acetyl d-lyxo-phytosphingosine. Tetrahedron Letters, 52, 6076-6079. DOI: 10.1016/j.tetlet.2011.08.170.
    • (2011) Tetrahedron Letters , vol.52 , pp. 6076-6079
    • Rao, G.S.1    Rao, B.V.2
  • 39
    • 33750630401 scopus 로고    scopus 로고
    • Highly efficient stereoselective synthesis of Derythro-sphingosine and d-lyxo-phytosphingosine
    • 10.1016/j.tet.2006.08.049 1:CAS:528:DC%2BD28XhtFyqsb%2FE
    • Righi, G., Ciambrone, S., D'Achille, C., Leonelli, A., & Bonini, C. (2006). Highly efficient stereoselective synthesis of Derythro-sphingosine and d-lyxo-phytosphingosine. Tetrahedron, 62, 11821-11826. DOI: 10.1016/j.tet.2006. 08.049.
    • (2006) Tetrahedron , vol.62 , pp. 11821-11826
    • Righi, G.1    Ciambrone, S.2    D'Achille, C.3    Leonelli, A.4    Bonini, C.5
  • 40
    • 0033607691 scopus 로고    scopus 로고
    • Phytosphingosines a facile synthesis and spectroscopic protocol for configuration assignment
    • 10.1016/S0040-4020(99)00839-X 1:CAS:528:DyaK1MXntlGqtbY%3D
    • Shirota, O., Nakanishi, K., & Berova, N. (1999). Phytosphingosines a facile synthesis and spectroscopic protocol for configuration assignment. Tetrahedron, 55, 13643-13658. DOI: 10.1016/s0040-4020(99)00839-x.
    • (1999) Tetrahedron , vol.55 , pp. 13643-13658
    • Shirota, O.1    Nakanishi, K.2    Berova, N.3
  • 41
    • 4444380439 scopus 로고    scopus 로고
    • 3N as a conveniet tool for the stereochemical interconversion of the hydroxyl group in N-acetyl 1,3-aminoalcohols. Asymmetric synthesis of N-acetyl l-xylo- and l-arabino-phytosphingosines
    • 10.1016/j.tetlet.2004.08.030 1:CAS:528:DC%2BD2cXnt12ktr0%3D
    • 3N as a conveniet tool for the stereochemical interconversion of the hydroxyl group in N-acetyl 1,3-aminoalcohols. Asymmetric synthesis of N-acetyl l-xylo- and l-arabino-phytosphingosines. Tetrahedron Letters, 45, 7239-7242. DOI: 10.1016/j.tetlet.2004.08.030.
    • (2004) Tetrahedron Letters , vol.45 , pp. 7239-7242
    • Singh, O.V.1    Kampf, D.J.2    Han, H.3
  • 42
    • 0032571231 scopus 로고    scopus 로고
    • Heatinduced elevation of ceramide in Saccharomyces cerevisiae via de novo synthesis
    • 10.1074/jbc.273.13.7235 1:CAS:528:DyaK1cXit1emtLk%3D
    • Wells, G. B., Dickson, R. C., & Lester, R. L. (1998). Heatinduced elevation of ceramide in Saccharomyces cerevisiae via de novo synthesis. The Journal of Biological Chemistry, 273, 7235-7243. DOI: 10.1074/jbc.273.13.7235.
    • (1998) The Journal of Biological Chemistry , vol.273 , pp. 7235-7243
    • Wells, G.B.1    Dickson, R.C.2    Lester, R.L.3


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