2-(4-allyloxyphenyl)ethyl 2,3,6-tri-O-chloroacetyl-β-D-glucopyranoside | 190123-29-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-allyloxyphenyl)ethyl 2,3,6-tri-O-chloroacetyl-β-D-glucopyranoside
• CAS: 190123-29-6
• 化学式: C₂₃H₂₇Cl₃O₁₀
• 分子量: 569.82
• InChiKey: RSGTYPZBTOCTKN-UJGPHIHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  36.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  126.82
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-(4-allyloxyphenyl)ethyl 2,3,6-tri-O-chloroacetyl-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 氨 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 3.5h， 生成 2-(3-methoxy-4-allyloxyphenyl)ethyl-4-Ο-(E)-4-Allyloxycaffeoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Total synthesis of the phenylpropanoid glycoside, grayanoside A

  摘要：

  Grayanoside A, 2-(4-hydroxyphenyl)ethyl 6-O-feruloyl-beta-D-glucopyranoside, was synthesized for the first time by using chloroacetyl groups for the protection of hydroxy functions. 2-(4-Allyloxyphenyl)ethyl 4-O-[(4-O-allyl)feruloyl]-2,3,6-tri-O-chloroacetyl-beta-D-glucopyranoside (12) was synthesized from 2-(4-allyloxyphenyl)ethyl 4,6-O-benzylidene-beta-D-glucopyranoside (8) in four steps with the goal of preparing syringalide B. It was found, however, that the feruloyl group migrated from the 4- to the 6-position of the glycopyranoside during the deprotection of 12. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00032-3
• 作为产物：
  描述：

  4-(烯丙氧基)-1-溴苯 在 sodium methylate 、 对甲苯磺酸 、 magnesium 、 原甲酸三乙酯 、 silver carbonate 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 硝基甲烷 、 二氯甲烷 、 溶剂黄146 、 苯 为溶剂， 反应 26.0h， 生成 2-(4-allyloxyphenyl)ethyl 2,3,6-tri-O-chloroacetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Total synthesis of the phenylpropanoid glycoside, grayanoside A

  摘要：

  Grayanoside A, 2-(4-hydroxyphenyl)ethyl 6-O-feruloyl-beta-D-glucopyranoside, was synthesized for the first time by using chloroacetyl groups for the protection of hydroxy functions. 2-(4-Allyloxyphenyl)ethyl 4-O-[(4-O-allyl)feruloyl]-2,3,6-tri-O-chloroacetyl-beta-D-glucopyranoside (12) was synthesized from 2-(4-allyloxyphenyl)ethyl 4,6-O-benzylidene-beta-D-glucopyranoside (8) in four steps with the goal of preparing syringalide B. It was found, however, that the feruloyl group migrated from the 4- to the 6-position of the glycopyranoside during the deprotection of 12. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00032-3