NOVEL PARTIAL PROTECTIONS OF 1,6-ANHYDRO-BETA-LACTOSE

被引：7

作者：

MORIKAWA, A ^{[1
]}

KUZUHARA, H ^{[1
]}

机构：

[1] INST PHYS & CHEM RES,WAKO,SAITAMA 35101,JAPAN

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 1990年 / 9卷 / 2-3期

关键词：

D O I：

10.1080/07328309008543825

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

1,6-Anhydro-β-lactose (3) was prepared as its peracetate (2) from lactose monohydrate via its pentachlorophenyl β-lactoside derivative in 49% overall yield. Treatment of the 4e,6*-0-benzylidene derivative of 3 with 1.2 mol. equiv. of 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane gave two cyclic silyl ethers, the 2’'-O-silyl and the 2,3:2',3’-di-0-silyl ethers, in the ratio of ca. 2:1. Cyclohexylidenation of 3 at 50 °C with excess of 1,1-dimethoxycyclohexane and trace of protic acid gave the 2',3':4,,6I- and the 2,2':3',4'-di-0-cyclohexylidene derivatives, whereas a similar reaction at 90–110 °C resulted in the 3,2':3',4'-di-0-cyclohexylidene derivative. © 1990, Taylor & Francis Group, LLC. All rights reserved.

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页码：167 / 179

页数：13

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