The Utility of a 3-O-Allyl Group as a Protective Group for Ring-Opening Polymerization of -D-Glucopyra
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- 作者：Makoto Karakawa ; Hiroshi Kamitakahara ; Toshiyuki Takano ; and Fumiaki Nakatsubo
- 刊名：Biomacromolecules
- 出版年：2002
- 出版时间：May 2002
- 年：2002
- 卷：3
- 期：3
- 页码：538 - 546
- 全文大小：135K
- 年卷期：v.3,no.3(May 2002)
- ISSN：1526-4602
文摘
To clarify the utility as a protective group of 3-O-allyl group on ring-opening polymerization of
-D-glucopyranose 1,2,4-orthopivalate derivatives, four orthopivalate derivatives, 3-O-allyl-6-O-pivaloyl-(1), 3-O-allyl-6-O-benzyl- (2), 3,6-di-O-allyl- (3), and 3-O-allyl-6-O-methyl--D-glucopyranose 1,2,4-orthopivalates (4), were selected as starting monomers and were polymerized under -30 
C in CH2Cl2using BF3·Et2O as a catalyst. All the orthopivalate derivatives 1-4 were found to give stereoregularpolysaccharides, (1
4)-
-D-glucopyranans. Thus, it was concluded that the allyl group as a protective groupat 3-O position of glucose othropivalate is acceptable to yield stereoregular (14)--D-glucopyranans,cellulose derivatives.
-D-glucopyranose 1,2,4-orthopivalate derivatives, four orthopivalate derivatives, 3-O-allyl-6-O-pivaloyl-(1), 3-O-allyl-6-O-benzyl- (2), 3,6-di-O-allyl- (3), and 3-O-allyl-6-O-methyl--D-glucopyranose 1,2,4-orthopivalates (4), were selected as starting monomers and were polymerized under -30 C in CH2Cl2using BF3·Et2O as a catalyst. All the orthopivalate derivatives 1-4 were found to give stereoregularpolysaccharides, (14)--D-glucopyranans. Thus, it was concluded that the allyl group as a protective groupat 3-O position of glucose othropivalate is acceptable to yield stereoregular (14)--D-glucopyranans,cellulose derivatives.