A NOVEL ENTRY INTO CYCLOPRONATED SUGAR AMINO-ACIDS

被引：0

作者：

FAKHARUZZAMAN ^{[1
]}

FATIMA, A ^{[1
]}

MALIK, A ^{[1
]}

VOELTER, W ^{[1
]}

机构：

[1] UNIV TUBINGEN, INST PHYSIOL CHEM, PHYS BIOCHEM ABT, D-72076 TUBINGEN, GERMANY

来源：

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES | 1994年 / 49卷 / 10期

关键词：

ANHYDRO SUGARS; SUGAR TRIFLATES; CYCLOPROPANATED SUGAR AMINO ACIDS;

D O I：

暂无

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Reaction of sugar triflates (1) and (2) with tert-butyl cyanoacetate in presence of sodium hydride affords the cyclopropanated sugars (3) and (4), followed by selective hydrolysis of the ester group to free acids (5) and (6), respectively. Couplings of (5) and (6) with protected glycine and L-alanine lead to cyclopropanated sugar amino acids (7-10). The coupling of 6 with benzyl 3,4-(''exo''-aminomethyl)methano-3,4-dideoxy-beta-L-arabinopyranoside (11) furnished benzyl 3,4-[(C-cyano-amido)methano-(benzyl 3,4-(''exo''-methylene)methano-3,4-dideoxy-beta-L-arabinopyranosido)]-3,4-dideoxy-beta-L-arbinopyranoside (12), suggesting an ''exo'' orientation of the ester group in 3 and 4.

引用

页码：1434 / 1438

页数：5

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