Synthesis of S-linked glycosyl amino acids in aqueous solution with unprotected carbohydrates

被引:46
作者
Cohen, SB [1 ]
Halcomb, RL [1 ]
机构
[1] Univ Colorado, Dept Chem & Biochem, Boulder, CO 80309 USA
关键词
D O I
10.1021/ol006908b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The cyclic sulfamidate 5 was synthesized in 60% overall yield from L-serine benzyl ester, Compound 5 reacted cleanly with the sodium thiolate salt of a variety of unprotected 1-thio sugars in aqueous buffer to afford the corresponding S-linked amino acid glycoconjugates in good yields after hydrolysis of the N-sulfates.
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收藏
页码:405 / 407
页数:3
相关论文
共 26 条
[1]   Synthesis of a thio-analogue of Lewis X by regioselective opening of cyclic sulfamidates [J].
Aguilera, B ;
Fernández-Mayoralas, A .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) :2719-2723
[2]   Synthesis of S-linked thiooligosaccharide analogues of Nod factors.: Part 1:: selectively N-protected 4-thiochitobiose precursors [J].
Auzanneau, FI ;
Bennis, K ;
Fanton, E ;
Promé, D ;
Defaye, J ;
Gelas, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (21) :3629-3635
[3]   CYCLIC SULPHAMIDATES - NEW SYNTHETIC PRECURSORS FOR BETA-FUNCTIONALIZED ALPHA-AMINO-ACIDS [J].
BALDWIN, JE ;
SPIVEY, AC ;
SCHOFIELD, CJ .
TETRAHEDRON-ASYMMETRY, 1990, 1 (12) :881-884
[4]   RULES FOR RING-CLOSURE [J].
BALDWIN, JE .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736
[5]   Generation of unnatural α,α-disubstituted amino acid derivatives from cyclic sulfamidates [J].
Boulton, LT ;
Stock, HT ;
Raphy, J ;
Horwell, DC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (11) :1421-1429
[6]  
DAVIS NJ, 1991, TETRAHEDRON LETT, V32, P6739
[7]   Synthesis of a thio-linked Lewis A (Lea) epitope [J].
Eisele, T ;
Windmüller, R ;
Schmidt, RR .
CARBOHYDRATE RESEARCH, 1998, 306 (1-2) :81-91
[8]  
Fernández JMG, 1998, J ORG CHEM, V63, P3572
[9]   STEREOSELECTIVE THIOGLYCOSES SYNTHESIS .12. A SIMPLE PREPARATION OF 2,3,4,6-TETRA-O-ACETYL-1-S-ACETYL-1-THIO-ALPHA-D-GLUCOPYRANOSE [J].
GADELLE, A ;
DEFAYE, J ;
PEDERSEN, C .
CARBOHYDRATE RESEARCH, 1990, 200 :497-498
[10]   VICINAL DIOL CYCLIC SULFATES - LIKE EPOXIDES ONLY MORE REACTIVE [J].
GAO, Y ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (22) :7538-7539