(1→4)连接的半乳糖醛酸三糖、一种推测的植物创伤激素及其立体异构体的合成。
Synthesis of (1----4)-linked galacturonic acid trisaccharides, a proposed plant wound-hormone and a stereoisomer.
作者信息
Nakahara Y, Ogawa T
机构信息
RIKEN, Institute of Physical and Chemical Research, Saitama, Japan.
出版信息
Carbohydr Res. 1990 Apr 25;200:363-75. doi: 10.1016/0008-6215(90)84203-7.
Syntheses of alpha-GalA-(1----4)-alpha-GalA-(1----4)-GalA, a proposed plant wound-hormone, and its stereoisomer beta-GalA-(1----4)-alpha-GalA-(1----4)-GalA are described. The key intermediates, tert-butyldiphenylsilyl O-(6-O-acetyl-2,3,4-tri-O-benzyl-alpha-D-galactopyranosyl)-(1----4)-O-(6 -O- acetyl-2,3-di-O-benzyl-alpha-D-galactopyranosyl)-(1----4)-6-O-acetyl-2,3 -di-O- benzyl-beta-D-galactopyranoside and tert-butyldiphenylsilyl O-(6-O-acetyl-2,3,4-tri-O-benzyl-beta-D-galactopyranosyl)-(1----4)-O-(6- O- acetyl-2,3-di-O-benzyl-alpha-D-galactopyranosyl)-(1----4)-6-O-acetyl-2,3 -di-O- benzyl-beta-D-galactopyranoside, were prepared by stereoselective alpha-glycosylation of tert-butyldiphenylsilyl 6-O-acetyl-2,3-di-O-benzyl-beta-D-galactopyranoside with O-(6-O-acetyl-2,3,4-tri-O-benzyl-alpha-D-galactopyranosyl)-(1----4)-6-O- acetyl-2,3-di-O-benzyl-D-galactopyranosyl fluoride and O-(6-O-acetyl-2,3,4-tri-O-benzyl-beta-D-galactopyranosyl)-(1----4)-6-O-a cetyl- 2,3-di-O-benzyl-D-galactopyranosyl fluoride, respectively. The corresponding beta isomers were minor products. Characteristic features in the n.m.r. data of the key intermediates are discussed.
本文描述了一种假定的植物创伤激素α-GalA-(1→4)-α-GalA-(1→4)-GalA及其立体异构体β-GalA-(1→4)-α-GalA-(1→4)-GalA的合成。关键中间体叔丁基二苯基甲硅烷基O-(6-O-乙酰基-2,3,4-三-O-苄基-α-D-吡喃半乳糖基)-(1→4)-O-(6-O-乙酰基-2,3-二-O-苄基-α-D-吡喃半乳糖基)-(1→4)-6-O-乙酰基-2,3-二-O-苄基-β-D-吡喃半乳糖苷和叔丁基二苯基甲硅烷基O-(6-O-乙酰基-2,3,4-三-O-苄基-β-D-吡喃半乳糖基)-(1→4)-O-(6-O-乙酰基-2,3-二-O-苄基-α-D-吡喃半乳糖基)-(1→4)-6-O-乙酰基-2,3-二-O-苄基-β-D-吡喃半乳糖苷分别通过叔丁基二苯基甲硅烷基6-O-乙酰基-2,3-二-O-苄基-β-D-吡喃半乳糖苷与O-(6-O-乙酰基-2,3,4-三-O-苄基-α-D-吡喃半乳糖基)-(1→4)-6-O-乙酰基-2,3-二-O-苄基-D-吡喃半乳糖基氟化物和O-(6-O-乙酰基-2,3,4-三-O-苄基-β-D-吡喃半乳糖基)-(1→4)-6-O-乙酰基-2,3-二-O-苄基-D-吡喃半乳糖基氟化物的立体选择性α-糖基化反应制备。相应的β异构体是次要产物。讨论了关键中间体核磁共振数据的特征。
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