메뉴 건너뛰기




Volumn , Issue 6, 2003, Pages 894-898

Stereoselective preparation of chiral building blocks having 1,3-syn-dimethyl group from D-glucose

Author keywords

Chelation control; Chiral building block; Non chelation control; Regioselectivity; Stereoselectivity

Indexed keywords

2 METHOXY 3,5 DIMETHYL TETRAHYDRO 2H PYRAN 6 CARBALDEHYDE; ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; EPOXIDE; GLUCOSE DERIVATIVE; MAGNESIUM CHLORIDE; METHYL GROUP; SODIUM DERIVATIVE; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037690733     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (3)

References (26)
  • 1
    • 0037781727 scopus 로고
    • Makurorido Koseibushitsu
    • Ohno, M.; Ohmura, S., Eds.; Tokyo Kagakudojinn: Tokyo
    • For reviews of macrolide antibiotics, see for example: (a) Tatsuta, K. Makurorido Koseibushitsu, In Koseibushitsu no Saisentan; Ohno, M.; Ohmura, S., Eds.; Tokyo Kagakudojinn: Tokyo, 1987, 252-281. (b) Paterson, I.; Mansuri, M. M. Tetrahedron 1985, 41, 3569. (c) Norcross, R. D.; Paterson, I. Chem. Rev. 1995, 95, 2041. (d) Ohmura, S. Macrolide Antibiotics: Chemistry, Biology, and Practice, 2nd ed; Academic Press: New York, 2002,.
    • (1987) Koseibushitsu no Saisentan , pp. 252-281
    • Tatsuta, K.1
  • 2
    • 0021880919 scopus 로고
    • For reviews of macrolide antibiotics, see for example: (a) Tatsuta, K. Makurorido Koseibushitsu, In Koseibushitsu no Saisentan; Ohno, M.; Ohmura, S., Eds.; Tokyo Kagakudojinn: Tokyo, 1987, 252-281. (b) Paterson, I.; Mansuri, M. M. Tetrahedron 1985, 41, 3569. (c) Norcross, R. D.; Paterson, I. Chem. Rev. 1995, 95, 2041. (d) Ohmura, S. Macrolide Antibiotics: Chemistry, Biology, and Practice, 2nd ed; Academic Press: New York, 2002,.
    • (1985) Tetrahedron , vol.41 , pp. 3569
    • Paterson, I.1    Mansuri, M.M.2
  • 3
    • 0001399971 scopus 로고
    • For reviews of macrolide antibiotics, see for example: (a) Tatsuta, K. Makurorido Koseibushitsu, In Koseibushitsu no Saisentan; Ohno, M.; Ohmura, S., Eds.; Tokyo Kagakudojinn: Tokyo, 1987, 252-281. (b) Paterson, I.; Mansuri, M. M. Tetrahedron 1985, 41, 3569. (c) Norcross, R. D.; Paterson, I. Chem. Rev. 1995, 95, 2041. (d) Ohmura, S. Macrolide Antibiotics: Chemistry, Biology, and Practice, 2nd ed; Academic Press: New York, 2002,.
    • (1995) Chem. Rev. , vol.95 , pp. 2041
    • Norcross, R.D.1    Paterson, I.2
  • 4
    • 0003661444 scopus 로고    scopus 로고
    • Academic Press: New York
    • For reviews of macrolide antibiotics, see for example: (a) Tatsuta, K. Makurorido Koseibushitsu, In Koseibushitsu no Saisentan; Ohno, M.; Ohmura, S., Eds.; Tokyo Kagakudojinn: Tokyo, 1987, 252-281. (b) Paterson, I.; Mansuri, M. M. Tetrahedron 1985, 41, 3569. (c) Norcross, R. D.; Paterson, I. Chem. Rev. 1995, 95, 2041. (d) Ohmura, S. Macrolide Antibiotics: Chemistry, Biology, and Practice, 2nd ed; Academic Press: New York, 2002,.
    • (2002) Macrolide Antibiotics: Chemistry, Biology, and Practice, 2nd Ed.
    • Ohmura, S.1
  • 6
    • 0004285331 scopus 로고    scopus 로고
    • John Wiley & Sons, Inc.: New York
    • See for example: (a) Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergamon Press: Oxford, 1983. (b) Bols, M. Carbohydrate Building Blocks; John Wiley & Sons, Inc.: New York, 1996,.
    • (1996) Carbohydrate Building Blocks
    • Bols, M.1
  • 7
    • 0038119359 scopus 로고
    • For the preparation of 4a and 4b, see: (a) Svirudov, A. F.; Yashunskii, D. V.; Ermolenko, M. S.; Kochetkov, N. K. Izvestiya Akademii Nauk SSSR, Seriya Kimicheskaya 1984, 723. (b) Hodges, P. J.; Procter, G. Tetrahedron Lett. 1985, 26, 4111; and refs therein. (c) Wakamatsu, T.; Nakamura, H.; Nishikimi, Y.; Yoshida, K.; Noda, T.; Taniguchi, M.; Ban, Y. Tetrahedron Lett. 1986, 27, 6071. (d) Nakamura, H.; Arata, K.; Wakamatsu, T.; Ban, Y.; Shibasaki, M. Chem. Pharm. Bull. 1990, 38, 2435. (e) Magdzinski, L.; Fraser-Reid, B. Can. J. Chem. 1988, 66, 2819. (f) See also: Edwards, M. P.; Ley, S. V.; Lister, S. G.; Palmer, B. D. J. Chem. Soc., Chem. Commun. 1983, 630.
    • (1984) Izvestiya Akademii Nauk SSSR, Seriya Kimicheskaya , pp. 723
    • Svirudov, A.F.1    Yashunskii, D.V.2    Ermolenko, M.S.3    Kochetkov, N.K.4
  • 8
    • 0038458547 scopus 로고
    • and refs therein
    • For the preparation of 4a and 4b, see: (a) Svirudov, A. F.; Yashunskii, D. V.; Ermolenko, M. S.; Kochetkov, N. K. Izvestiya Akademii Nauk SSSR, Seriya Kimicheskaya 1984, 723. (b) Hodges, P. J.; Procter, G. Tetrahedron Lett. 1985, 26, 4111; and refs therein. (c) Wakamatsu, T.; Nakamura, H.; Nishikimi, Y.; Yoshida, K.; Noda, T.; Taniguchi, M.; Ban, Y. Tetrahedron Lett. 1986, 27, 6071. (d) Nakamura, H.; Arata, K.; Wakamatsu, T.; Ban, Y.; Shibasaki, M. Chem. Pharm. Bull. 1990, 38, 2435. (e) Magdzinski, L.; Fraser-Reid, B. Can. J. Chem. 1988, 66, 2819. (f) See also: Edwards, M. P.; Ley, S. V.; Lister, S. G.; Palmer, B. D. J. Chem. Soc., Chem. Commun. 1983, 630.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 4111
    • Hodges, P.J.1    Procter, G.2
  • 9
    • 0038458550 scopus 로고
    • For the preparation of 4a and 4b, see: (a) Svirudov, A. F.; Yashunskii, D. V.; Ermolenko, M. S.; Kochetkov, N. K. Izvestiya Akademii Nauk SSSR, Seriya Kimicheskaya 1984, 723. (b) Hodges, P. J.; Procter, G. Tetrahedron Lett. 1985, 26, 4111; and refs therein. (c) Wakamatsu, T.; Nakamura, H.; Nishikimi, Y.; Yoshida, K.; Noda, T.; Taniguchi, M.; Ban, Y. Tetrahedron Lett. 1986, 27, 6071. (d) Nakamura, H.; Arata, K.; Wakamatsu, T.; Ban, Y.; Shibasaki, M. Chem. Pharm. Bull. 1990, 38, 2435. (e) Magdzinski, L.; Fraser-Reid, B. Can. J. Chem. 1988, 66, 2819. (f) See also: Edwards, M. P.; Ley, S. V.; Lister, S. G.; Palmer, B. D. J. Chem. Soc., Chem. Commun. 1983, 630.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 6071
    • Wakamatsu, T.1    Nakamura, H.2    Nishikimi, Y.3    Yoshida, K.4    Noda, T.5    Taniguchi, M.6    Ban, Y.7
  • 10
    • 0024999836 scopus 로고
    • For the preparation of 4a and 4b, see: (a) Svirudov, A. F.; Yashunskii, D. V.; Ermolenko, M. S.; Kochetkov, N. K. Izvestiya Akademii Nauk SSSR, Seriya Kimicheskaya 1984, 723. (b) Hodges, P. J.; Procter, G. Tetrahedron Lett. 1985, 26, 4111; and refs therein. (c) Wakamatsu, T.; Nakamura, H.; Nishikimi, Y.; Yoshida, K.; Noda, T.; Taniguchi, M.; Ban, Y. Tetrahedron Lett. 1986, 27, 6071. (d) Nakamura, H.; Arata, K.; Wakamatsu, T.; Ban, Y.; Shibasaki, M. Chem. Pharm. Bull. 1990, 38, 2435. (e) Magdzinski, L.; Fraser-Reid, B. Can. J. Chem. 1988, 66, 2819. (f) See also: Edwards, M. P.; Ley, S. V.; Lister, S. G.; Palmer, B. D. J. Chem. Soc., Chem. Commun. 1983, 630.
    • (1990) Chem. Pharm. Bull. , vol.38 , pp. 2435
    • Nakamura, H.1    Arata, K.2    Wakamatsu, T.3    Ban, Y.4    Shibasaki, M.5
  • 11
    • 0038458549 scopus 로고
    • For the preparation of 4a and 4b, see: (a) Svirudov, A. F.; Yashunskii, D. V.; Ermolenko, M. S.; Kochetkov, N. K. Izvestiya Akademii Nauk SSSR, Seriya Kimicheskaya 1984, 723. (b) Hodges, P. J.; Procter, G. Tetrahedron Lett. 1985, 26, 4111; and refs therein. (c) Wakamatsu, T.; Nakamura, H.; Nishikimi, Y.; Yoshida, K.; Noda, T.; Taniguchi, M.; Ban, Y. Tetrahedron Lett. 1986, 27, 6071. (d) Nakamura, H.; Arata, K.; Wakamatsu, T.; Ban, Y.; Shibasaki, M. Chem. Pharm. Bull. 1990, 38, 2435. (e) Magdzinski, L.; Fraser-Reid, B. Can. J. Chem. 1988, 66, 2819. (f) See also: Edwards, M. P.; Ley, S. V.; Lister, S. G.; Palmer, B. D. J. Chem. Soc., Chem. Commun. 1983, 630.
    • (1988) Can. J. Chem. , vol.66 , pp. 2819
    • Magdzinski, L.1    Fraser-Reid, B.2
  • 12
    • 0020523996 scopus 로고
    • For the preparation of 4a and 4b, see: (a) Svirudov, A. F.; Yashunskii, D. V.; Ermolenko, M. S.; Kochetkov, N. K. Izvestiya Akademii Nauk SSSR, Seriya Kimicheskaya 1984, 723. (b) Hodges, P. J.; Procter, G. Tetrahedron Lett. 1985, 26, 4111; and refs therein. (c) Wakamatsu, T.; Nakamura, H.; Nishikimi, Y.; Yoshida, K.; Noda, T.; Taniguchi, M.; Ban, Y. Tetrahedron Lett. 1986, 27, 6071. (d) Nakamura, H.; Arata, K.; Wakamatsu, T.; Ban, Y.; Shibasaki, M. Chem. Pharm. Bull. 1990, 38, 2435. (e) Magdzinski, L.; Fraser-Reid, B. Can. J. Chem. 1988, 66, 2819. (f) See also: Edwards, M. P.; Ley, S. V.; Lister, S. G.; Palmer, B. D. J. Chem. Soc., Chem. Commun. 1983, 630.
    • (1983) J. Chem. Soc., Chem. Commun. , pp. 630
    • Edwards, M.P.1    Ley, S.V.2    Lister, S.G.3    Palmer, B.D.4
  • 16
    • 0038796288 scopus 로고    scopus 로고
    • note
    • 3) for 3: δ(ppm) 1.12 (d, C2-Me, J = 9.6 Hz), 1.27 (d, C4-Me, J = 7.7 Hz), 4.25 (d, C5-H, J = 5.5 Hz), 3.80 (dd, C6-Ha, J = 5.6 Hz, 6.9 Hz), and 3.87 (dd, C6-Hb).
  • 17
    • 0037781724 scopus 로고
    • For the preparation of α-7 and analogous compounds, see: (a) Isobe, M.; Ichikawa, Y.; Goto, T. Tetrahedron Lett. 1981, 22, 4287. (b) Jarosz, S.; Fraser-Reid, B. Tetrahedron Lett. 1981, 27, 2533. (c) Kawauchi, N.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1987, 60, 1441. (d) Chen, S.-H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 5834.
    • (1981) Tetrahedron Lett. , vol.22 , pp. 4287
    • Isobe, M.1    Ichikawa, Y.2    Goto, T.3
  • 18
    • 0037781723 scopus 로고
    • For the preparation of α-7 and analogous compounds, see: (a) Isobe, M.; Ichikawa, Y.; Goto, T. Tetrahedron Lett. 1981, 22, 4287. (b) Jarosz, S.; Fraser-Reid, B. Tetrahedron Lett. 1981, 27, 2533. (c) Kawauchi, N.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1987, 60, 1441. (d) Chen, S.-H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 5834.
    • (1981) Tetrahedron Lett. , vol.27 , pp. 2533
    • Jarosz, S.1    Fraser-Reid, B.2
  • 19
    • 0037781722 scopus 로고
    • For the preparation of α-7 and analogous compounds, see: (a) Isobe, M.; Ichikawa, Y.; Goto, T. Tetrahedron Lett. 1981, 22, 4287. (b) Jarosz, S.; Fraser-Reid, B. Tetrahedron Lett. 1981, 27, 2533. (c) Kawauchi, N.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1987, 60, 1441. (d) Chen, S.-H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 5834.
    • (1987) Bull. Chem. Soc. Jpn. , vol.60 , pp. 1441
    • Kawauchi, N.1    Hashimoto, H.2
  • 20
    • 0026003109 scopus 로고
    • For the preparation of α-7 and analogous compounds, see: (a) Isobe, M.; Ichikawa, Y.; Goto, T. Tetrahedron Lett. 1981, 22, 4287. (b) Jarosz, S.; Fraser-Reid, B. Tetrahedron Lett. 1981, 27, 2533. (c) Kawauchi, N.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1987, 60, 1441. (d) Chen, S.-H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 5834.
    • (1991) J. Org. Chem. , vol.56 , pp. 5834
    • Chen, S.-H.1    Horvath, R.F.2    Joglar, J.3    Fisher, M.J.4    Danishefsky, S.J.5
  • 24
    • 0037781726 scopus 로고    scopus 로고
    • note
    • See Abstract.
  • 26
    • 0038119360 scopus 로고    scopus 로고
    • note
    • Yields were not optimized.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.