Substituent effect on ring-opening polymerization of regioselectively acylated α-D-glucopyranose 1,2,4-orthopivalate derivatives
Substituent effect on ring-opening polymerization of regioselectively acylated α-D-glucopyranose 1,2,4-orthopivalate derivatives
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取代基对区域选择性酰化α-D-吡喃葡萄糖1,2,4-原戊酸衍生物开环聚合的影响
DOI：
10.1021/ma960488h
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发表时间：
1996
期刊：
影响因子：
5.5
通讯作者：
F. Nakatsubo
中科院分区：
文献类型：
--
作者：
Hiroshi Kamitakahara;M. Hori;F. Nakatsubo
为了研究 3-O 和 6-O 位上的取代基对开环聚合的影响，3,6-二-O-苄基-α-d-吡喃葡萄糖 1,2,4-原戊酸 (1)、3-O-苄基-6-O-新戊酰-α-d-吡喃葡萄糖 1,2,4-原戊酸 (2)， 选择6-O-苄基-3-O-新戊酰-α-d-吡喃葡萄糖1,2,4-原戊酸(3)和3,6-二-O-新戊酰-α-d-吡喃葡萄糖1,2,4-原戊酸(4)作为起始单体，并在各种反应条件下聚合。从之前报道的单体1的结果和本研究中单体2−4的结果得出结论，3-O位的苄基对于产生有规立构的(1→4)-β-d-吡喃葡萄糖衍生物，即纤维素衍生物是必不可少的。讨论了开环聚合的机理。
To investigate the substituent effects at the 3-O and 6-O positions on ring-opening polymerization, 3,6-di-O-benzyl-α-d-glucopyranose 1,2,4-orthopivalate (1), 3-O-benzyl-6-O-pivaloyl-α-d-glucopyranose 1,2,4-orthopivalate (2), 6-O-benzyl-3-O-pivaloyl-α-d-glucopyranose 1,2,4-orthopivalate (3), and 3,6-di-O-pivaloyl-α-d-glucopyranose 1,2,4-orthopivalate (4) were selected as starting monomers and were polymerized under various reaction conditions. It was concluded from the results of monomer 1 reported previously and from those of monomers 2−4 in our present study that the benzyl group at the 3-O position is indispensable for yielding stereoregular (1→4)-β-d-glucopyranan derivatives, i.e., cellulose derivatives. The mechanisms of ring-opening polymerizations are discussed.