Efficient, diastereoselective chemical synthesis of a β-mannopyranosyl phosphoisoprenoid

被引:20
作者
Crich, D [1 ]
Dudkin, V [1 ]
机构
[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA
关键词
D O I
10.1021/ol006725p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Tetrabutylammonium benzyl dihydrophytylphosphate was coupled to S-phenyl 2,3-di-O-benyl-4,6-O-benzylidene-1-thio-alpha -D-mannopyranoside S-oxide on activation with triflic anhydride in toluene at -78 degreesC to give the corresponding beta -mannosyl phosphate in 56% yield with no detectable formation of the alpha -anomer. Treatment with sodium in liquid ammonia then afforded the unprotected beta -mannosyl phosphoisoprenoid.
引用
收藏
页码:3941 / 3943
页数:3
相关论文
共 16 条
[1]   A solvation-assisted model for estimating anomeric reactivity. Predicted versus observed trends in hydrolysis of n-pentenyl glycosides [J].
Andrews, CW ;
Rodebaugh, R ;
FraserReid, B .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5280-5289
[2]   IDENTIFICATION OF THE APPARENT CARRIER IN MYCOLIC ACID SYNTHESIS [J].
BESRA, GS ;
SIEVERT, T ;
LEE, RE ;
SLAYDEN, RA ;
BRENNAN, PJ ;
TAKAYAMA, K .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (26) :12735-12739
[3]   STUDY OF C-13H COUPLING-CONSTANTS IN HEXOPYRANOSES [J].
BOCK, K ;
PEDERSEN, C .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1974, (03) :293-299
[4]   KEY SYNTHETIC ANALOGS OF BLEOMYCIN A(2) THAT DIRECTLY ADDRESS THE EFFECT AND ROLE OF THE DISACCHARIDE - DEMANNOSYLBLEOMYCIN A(2) AND ALPHA-D-MANNOPYRANOSYLDEGLYCOBLEOMYCIN A(2) [J].
BOGER, DL ;
TERAMOTO, S ;
ZHOU, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (28) :7344-7356
[5]   Are glycosyl triflates intermediates in the sulfoxide glycosylation method? A chemical and H-1, C-13, and F-19 NMR spectroscopic investigation [J].
Crich, D ;
Sun, SX .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (46) :11217-11223
[6]   Direct chemical synthesis of β-mannopyranosides and other glycosides via glycosyl triflates [J].
Crich, D ;
Sun, SX .
TETRAHEDRON, 1998, 54 (29) :8321-8348
[7]   Direct synthesis of beta-mannopyranosides by the sulfoxide method [J].
Crich, D ;
Sun, SX .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) :1198-1199
[8]   Direct formation of β-mannopyranosides and other hindered glycosides from thioglycosides [J].
Crich, D ;
Sun, SX .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (02) :435-436
[9]   Synthesis of glycosyl-1-phosphates via dehydrative glycosylation [J].
Garcia, BA ;
Gin, DY .
ORGANIC LETTERS, 2000, 2 (14) :2135-2138
[10]   Sulfenate intermediates in the sulfoxide glycosylation reaction [J].
Gildersleeve, J ;
Pascal, RA ;
Kahne, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (24) :5961-5969