4-methoxyphenyl 3,6-O-(o-xylylene)-D-glucopyranoside | 1181208-89-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl 3,6-O-(o-xylylene)-D-glucopyranoside
• 英文别名: 4-methoxyphenyl 3,6-O-(o-xylylene)-α-D-glucopyranoside；(1S,13R,15R,16R,17R)-15-(4-methoxyphenoxy)-2,11,14-trioxatricyclo[11.3.1.04,9]heptadeca-4,6,8-triene-16,17-diol
• CAS: 1181208-89-8
• 化学式: C₂₁H₂₄O₇
• 分子量: 388.417
• InChiKey: WKXRFXIYQZBBCD-XKRYSZRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-1,2-O-(S)-(1-ethoxyethylidene)-α-D-glucopyranose 在 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 17.0h， 生成 4-methoxyphenyl 3,6-O-(o-xylylene)-D-glucopyranoside 、 4-methoxyphenyl 3,6-O-(o-xylylene)-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of 3,6-O-(o-Xylylene)glucopyranosyl Fluoride, an Axial-Rich Glycosyl Donor of β-Glycosylation

  摘要：

  Despite the reported complete beta-selectivity in glycosylation with 2,4-di-O-benzyl-3,6-O-(o-xylylene)-glucopyranosyl fluoride, its preparation has been inefficient. This paper describes an improved route for the donor, including the formation of the 3,6-bridge on 1,2,4-orthoacetylglucose, the preparation of which was also refined, along with a discovered feature that the 3,6-bridged glucose prefers the furanose form. Although this feature made the synthesis of the desired glucopyranosyl donor difficult, application of thermal glycosylation solved the problem. With a modifiable intermediate, the improved availability of the donor would expand the applications.

  DOI：

  10.1021/jo401395h

文献信息

• 3, 6-O-BRIDGED PYRANOSE INVERSION COMPOUND AND PROCESS FOR PRODUCING B-O-PYRANOSIDE
  申请人：Yamada Hidetoshi

  公开号：US20100324275A1

  公开（公告）日：2010-12-23

  An object of the present invention is to provide a 3,6-O-bridged pyranose-inverted compound useful for being easy to produce β-O-pyranosides selectively. The 3,6-O-bridged pyranose-inverted compound according to the present invention is represented by General Formula (1): wherein R A and R B each represent hydrogen or are bonded to each other to form a benzene ring; one of R C and R D represents hydrogen and the other represents —OR 2 ; R 1 represents hydroxy or halogen; and R 2 and R 3 each represent a hydroxy-protecting group.

  本发明的一个目的是提供一种3,6-O-桥联吡喃糖倒置化合物，用于易于选择性地生产β-O-吡喃糖苷。根据本发明，3,6-O-桥联吡喃糖倒置化合物由通式（1）表示：其中RA和RB分别表示氢原子或结合在一起形成苯环；RC和RD中的一个表示氢原子，另一个表示—OR2；R1表示羟基或卤素；R2和R3各自表示一个羟基保护基团。
• US8445652B2
  申请人：——

  公开号：US8445652B2

  公开（公告）日：2013-05-21