메뉴 건너뛰기




Volumn 25, Issue 6, 2006, Pages 441-450

A facile, one-step conversion of 6-O-trityl and 6-O-TBDMS monosaccharides into the corresponding formate esters

Author keywords

Formate ester; Formic acid; O branched chain reactions; tert Butyldimethylsilyl; Trityl

Indexed keywords


EID: 33747094424     PISSN: 07328303     EISSN: 15322327     Source Type: Journal    
DOI: 10.1080/07328300600859668     Document Type: Article
Times cited : (9)

References (36)
  • 1
    • 0036199428 scopus 로고    scopus 로고
    • Regio- and stereoselective transformations of sucrose at the terminal positions
    • Jarosz, S.; Mach, M. Regio- and stereoselective transformations of sucrose at the terminal positions. Eur. J. Org. Chem. 2002, 769-780.
    • (2002) Eur. J. Org. Chem. , pp. 769-780
    • Jarosz, S.1    Mach, M.2
  • 2
    • 84971044414 scopus 로고
    • Tert-butyldimethylsilyl ethers of sucrose
    • Franke, F.; Guthrie, R.D. Tert-butyldimethylsilyl ethers of sucrose. Aust. J. Chem. 1977, 30, 639-647.
    • (1977) Aust. J. Chem. , vol.30 , pp. 639-647
    • Franke, F.1    Guthrie, R.D.2
  • 3
    • 0027999360 scopus 로고
    • Selective removal of phenolic and alcoholic silyl ethers
    • Prakash, C.; Saleh, S.; Blair, I.A. Selective removal of phenolic and alcoholic silyl ethers. Tetrahedron Lett. 1994, 35, 7565-7568.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 7565-7568
    • Prakash, C.1    Saleh, S.2    Blair, I.A.3
  • 4
    • 0031031125 scopus 로고    scopus 로고
    • A mild and efficient method for the selective cleavage of tertbutyldimethylsilyl ethers to alcohols
    • Maiti, G.; Roy, S.C. A mild and efficient method for the selective cleavage of tertbutyldimethylsilyl ethers to alcohols. Tetrahedron Lett. 1997, 38, 495-498.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 495-498
    • Maiti, G.1    Roy, S.C.2
  • 5
    • 0037178522 scopus 로고    scopus 로고
    • Mild and highly selective formyl protection of primary hydroxyl groups
    • DeLuca, L.; Giacomelli, G.; Porcheddu, A. Mild and highly selective formyl protection of primary hydroxyl groups. J. Org. Chem. 2002, 67, 5152-5155.
    • (2002) J. Org. Chem. , vol.67 , pp. 5152-5155
    • DeLuca, L.1    Giacomelli, G.2    Porcheddu, A.3
  • 6
    • 0000382918 scopus 로고
    • Preparation and methanolysis of uridine, 6-azauridine and 6-azacytidine O-formyl derivatives
    • Zemlicka, J.; Beranek, J.; Smrt, J. Preparation and methanolysis of uridine, 6-azauridine and 6-azacytidine O-formyl derivatives. Collect. Czech. Chem. Commun. 1962, 27, 2784.
    • (1962) Collect. Czech. Chem. Commun. , vol.27 , pp. 2784
    • Zemlicka, J.1    Beranek, J.2    Smrt, J.3
  • 7
    • 0014317796 scopus 로고
    • Methoxyacetyl as a protecting group in ribonucleoside chemistry
    • Reese, C.B.; Stewart, J.C.M. Methoxyacetyl as a protecting group in ribonucleoside chemistry. Tetrahedron Lett. 1968, 4273-4276.
    • (1968) Tetrahedron Lett. , pp. 4273-4276
    • Reese, C.B.1    Stewart, J.C.M.2
  • 10
    • 0001544907 scopus 로고
    • Short-step syntheses of (±)bazzanene and (±)trichodiene
    • Suda, M. Short-step syntheses of (±)bazzanene and (±)trichodiene. Tetrahedron Lett. 1982, 427-428.
    • (1982) Tetrahedron Lett. , pp. 427-428
    • Suda, M.1
  • 11
    • 0001074970 scopus 로고
    • Synthesis and highly regioselective diels-alder reaction of functionalized isoprenes involving a terminal alkoxy group and chemical modification of the resulting adducts
    • Mandai, T.; Osaka, K.; Kawagishi, M.; Kawada, M.; Otera, J. Synthesis and highly regioselective diels-alder reaction of functionalized isoprenes involving a terminal alkoxy group and chemical modification of the resulting adducts. J. Org. Chem. 1984, 49, 3595-3600.
    • (1984) J. Org. Chem. , vol.49 , pp. 3595-3600
    • Mandai, T.1    Osaka, K.2    Kawagishi, M.3    Kawada, M.4    Otera, J.5
  • 12
    • 0000054299 scopus 로고
    • Stereocontolled formation of cis and trans ring junctions in hydrindane and decalin systems by palladium-catalyzed regioselective hydrogenolysis of allylic formates
    • Mandai, T.; Matsumoto, T.; Kawada, M.; Tsuji, J. Stereocontolled formation of cis and trans ring junctions in hydrindane and decalin systems by palladium-catalyzed regioselective hydrogenolysis of allylic formates. J. Org. Chem. 1992, 57, 1326-1327.
    • (1992) J. Org. Chem. , vol.57 , pp. 1326-1327
    • Mandai, T.1    Matsumoto, T.2    Kawada, M.3    Tsuji, J.4
  • 13
    • 0001214141 scopus 로고
    • Regioselective palladium(II) catalysed hydroesterification of alkynes and alkynols using formate esters
    • Ali, B.E.; Alper, H. Regioselective palladium(II) catalysed hydroesterification of alkynes and alkynols using formate esters. J. Mol. Catal. A 1995, 96, 197-201.
    • (1995) J. Mol. Catal. A , vol.96 , pp. 197-201
    • Ali, B.E.1    Alper, H.2
  • 14
    • 0000164318 scopus 로고
    • Reaction of phosphoranes with formate esters. A new method for the synthesis of vinyl ethers
    • Subramanyam, V.; Silver, E.H. Reaction of phosphoranes with formate esters. A new method for the synthesis of vinyl ethers. J. Org. Chem. 1976, 41, 1272-1273.
    • (1976) J. Org. Chem. , vol.41 , pp. 1272-1273
    • Subramanyam, V.1    Silver, E.H.2
  • 16
    • 0029007649 scopus 로고
    • N-Formylbenzotriazole - A stable and convenient N-formylating and O-formylating agent
    • Katritzky, A.R.; Chang, H.X.; Yang, B. N-Formylbenzotriazole - a stable and convenient N-formylating and O-formylating agent. Synthesis 1995, 503-505.
    • (1995) Synthesis , pp. 503-505
    • Katritzky, A.R.1    Chang, H.X.2    Yang, B.3
  • 17
    • 84989453187 scopus 로고
    • General-method for the formylation of alcohols with dimethylformamide - An extension of the Vilsmeier-Haack reaction
    • Barluenga, J.; Campos, P.J.; Gonzales-Nunez, E.; Asensio, G. General-method for the formylation of alcohols with dimethylformamide - an extension of the Vilsmeier-Haack reaction. Synthesis 1985, 426-428.
    • (1985) Synthesis , pp. 426-428
    • Barluenga, J.1    Campos, P.J.2    Gonzales-Nunez, E.3    Asensio, G.4
  • 18
    • 33845282659 scopus 로고
    • Synthetic methods and reactions. 130. Formylating agents
    • Olah, G.A.; Ohannesian, L.; Arvanaghi, M. Synthetic methods and reactions. 130. Formylating agents. Chem. Rev. 1987, 87, 671-686.
    • (1987) Chem. Rev. , vol.87 , pp. 671-686
    • Olah, G.A.1    Ohannesian, L.2    Arvanaghi, M.3
  • 19
    • 0032575239 scopus 로고    scopus 로고
    • Acetylation and formylation of alcohols with triphenylphosphine and carbon tetrabromide in ethyl acetate or ethyl acetate or ethyl formate
    • Hagiwara, H.; Morohashi, K.; Sakai, H.; Suzuki, T.; Ando, M. Acetylation and formylation of alcohols with triphenylphosphine and carbon tetrabromide in ethyl acetate or ethyl acetate or ethyl formate. Tetrahedron 1998, 54, 5845-5852.
    • (1998) Tetrahedron , vol.54 , pp. 5845-5852
    • Hagiwara, H.1    Morohashi, K.2    Sakai, H.3    Suzuki, T.4    Ando, M.5
  • 21
    • 0035830522 scopus 로고    scopus 로고
    • 2O/DMF. Their unique and selective conversion to the corresponding C(6)-O-formates
    • 2O/DMF. Their unique and selective conversion to the corresponding C(6)-O-formates. J. Org. Chem. 2001, 66, 693-696.
    • (2001) J. Org. Chem. , vol.66 , pp. 693-696
    • Lellouche, J.P.1    Koeller, S.2
  • 22
    • 1442286541 scopus 로고    scopus 로고
    • Vilsmeier-Haack reagents. Novel electrophiles for the one-step formylation of O-silylated ethers to O-formates
    • Lellouche, J.P.; Kotlyar, V. Vilsmeier-Haack reagents. Novel electrophiles for the one-step formylation of O-silylated ethers to O-formates. Synlett. 2004, 3, 564-571.
    • (2004) Synlett. , vol.3 , pp. 564-571
    • Lellouche, J.P.1    Kotlyar, V.2
  • 24
    • 0021763503 scopus 로고
    • Synthesis and characterization of methyl 6-O-α- and -β-D-galactopyranosyl-β-D-galactopyranoside
    • Kovac, P.; Sokoloski, E.A.; Glaudemans, C.P.J. Synthesis and characterization of methyl 6-O-α- and -β-D-galactopyranosyl-β-D- galactopyranoside. Carbohydr. Res. 1984, 128, 101-110.
    • (1984) Carbohydr. Res. , vol.128 , pp. 101-110
    • Kovac, P.1    Sokoloski, E.A.2    Glaudemans, C.P.J.3
  • 25
    • 0000416806 scopus 로고
    • Methylation of carbohydrates bearing base-labile substituents, with diazomethane-boron trifluoride etherate
    • Gros, E.G.; Gruneiro, E.M. Methylation of carbohydrates bearing base-labile substituents, with diazomethane-boron trifluoride etherate. Carbohydr. Res. 1970, 14, 409-411.
    • (1970) Carbohydr. Res. , vol.14 , pp. 409-411
    • Gros, E.G.1    Gruneiro, E.M.2
  • 26
    • 0002997747 scopus 로고
    • Pelative reactivities of hydroxyl groups in carbohydrate derivatives. Specific nuclear magnetic resonance spectral assignments of acetyl groups in methyl α-D-glucopyranoside tetraacetate and related derivatives
    • Horton, D.; Lauterback, J.H. Pelative reactivities of hydroxyl groups in carbohydrate derivatives. Specific nuclear magnetic resonance spectral assignments of acetyl groups in methyl α-D-glucopyranoside tetraacetate and related derivatives. J. Org. Chem. 1969, 34, 86-92.
    • (1969) J. Org. Chem. , vol.34 , pp. 86-92
    • Horton, D.1    Lauterback, J.H.2
  • 27
    • 0000518373 scopus 로고
    • Rapid and selective detritylation of primary alcohols using formic acid
    • Bessodes, M.; Komiotis, D.; Antonakis, K. Rapid and selective detritylation of primary alcohols using formic acid. Tetrahedron Lett. 1986, 27, 579-580.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 579-580
    • Bessodes, M.1    Komiotis, D.2    Antonakis, K.3
  • 28
    • 37049042590 scopus 로고
    • The phosphobetaines: Preparation and properties
    • Trippet, S.; Walker, D.M. The phosphobetaines: preparation and properties. J. Chem. Soc. 1961, 1266-1272.
    • (1961) J. Chem. Soc. , pp. 1266-1272
    • Trippet, S.1    Walker, D.M.2
  • 29
    • 0034583249 scopus 로고    scopus 로고
    • Formylation of carbohydrates and the evolution of synthetic routes to artificial oligosacharides and glycoconjugates
    • Dondoni, A. Formylation of carbohydrates and the evolution of synthetic routes to artificial oligosacharides and glycoconjugates. Pure Appl. Chem. 2000, 72, 1577-1588.
    • (2000) Pure Appl. Chem. , vol.72 , pp. 1577-1588
    • Dondoni, A.1
  • 30
    • 0002600376 scopus 로고    scopus 로고
    • Preparation of long-chain esters of starch using fatty acid chlorides in the absence of an organic solvent
    • Aburto, J.; Alric, I.; Borredon, I. Preparation of long-chain esters of starch using fatty acid chlorides in the absence of an organic solvent. Starch/Starke 1999, 51, 132-135.
    • (1999) Starch/Starke , vol.51 , pp. 132-135
    • Aburto, J.1    Alric, I.2    Borredon, I.3
  • 32
    • 0030865641 scopus 로고    scopus 로고
    • Small molecules as structural and functional mimics of sialyl Lewis X tetrasaccharide in slectin inhibition: A remarkable enhancement of inhibition by additional negative charge and/or hydrophobic group
    • Wong, C.H.; Moris-Varas, F.; Hung, S.C.; Marron, T.G.; Lin, C.C.; Gong, K.W.; Weitz-Schmidt, G. Small molecules as structural and functional mimics of sialyl Lewis X tetrasaccharide in slectin inhibition: a remarkable enhancement of inhibition by additional negative charge and/or hydrophobic group. J. Am. Chem. Soc. 1997, 119, 8152-8158.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 8152-8158
    • Wong, C.H.1    Moris-Varas, F.2    Hung, S.C.3    Marron, T.G.4    Lin, C.C.5    Gong, K.W.6    Weitz-Schmidt, G.7
  • 33
    • 0030845782 scopus 로고    scopus 로고
    • O-glycosyl a-amino acids as building blocks for glycopeptide synthesis
    • Arsequell, G.; Valencia, G. O-glycosyl a-amino acids as building blocks for glycopeptide synthesis. Tetrahedron: Assymm. 1997, 8, 2839-2876.
    • (1997) Tetrahedron: Assymm. , vol.8 , pp. 2839-2876
    • Arsequell, G.1    Valencia, G.2
  • 34
    • 0032541645 scopus 로고    scopus 로고
    • Glycopeptides and glycoproteins: Focus on the glycosidic linkage
    • Taylor, C.M. Glycopeptides and glycoproteins: focus on the glycosidic linkage. Tetrahedron 1998, 54, 11317-11362.
    • (1998) Tetrahedron , vol.54 , pp. 11317-11362
    • Taylor, C.M.1
  • 35
    • 14744268646 scopus 로고    scopus 로고
    • Use of O-glycosylation in total synthesis
    • Pellissier, H. Use of O-glycosylation in total synthesis. Tetrahedron 2005, 61, 2947-2993.
    • (2005) Tetrahedron , vol.61 , pp. 2947-2993
    • Pellissier, H.1
  • 36
    • 15244360014 scopus 로고    scopus 로고
    • Synthesis and human NKT cell stimulating properties of 3-O-sulfo-α/β-galactosylceramides
    • Xing, G.W.; Wu, D.; Poles, M.A.; Horowitz, A.; Tsuji, M.; Ho, D.D.; Wong, C.H. Synthesis and human NKT cell stimulating properties of 3-O-sulfo-α/β-galactosylceramides. Bioorg. Med. Chem. 2005, 13, 2907-2916.
    • (2005) Bioorg. Med. Chem. , vol.13 , pp. 2907-2916
    • Xing, G.W.1    Wu, D.2    Poles, M.A.3    Horowitz, A.4    Tsuji, M.5    Ho, D.D.6    Wong, C.H.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.