Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(4-allyloxy-phenyl)-ethoxy]-tetrahydro-pyran-4-yl ester | 797041-00-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(4-allyloxy-phenyl)-ethoxy]-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[2-(4-prop-2-enoxyphenyl)ethoxy]oxan-2-yl]methyl acetate
• CAS: 797041-00-0
• 化学式: C₂₅H₃₂O₁₁
• 分子量: 508.522
• InChiKey: WHUSGCHWEDWLOQ-NHTNDUFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  36
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(4-allyloxy-phenyl)-ethoxy]-tetrahydro-pyran-4-yl ester 在 ammonium acetate 、 sodium methylate 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 22.0h， 生成
  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 magnesium 、 silver carbonate 作用下， 以 硝基甲烷 、 苯 为溶剂， 反应 12.0h， 生成 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(4-allyloxy-phenyl)-ethoxy]-tetrahydro-pyran-4-yl ester
  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

文献信息

• Short synthesis of phenylpropanoid glycosides calceolarioside-B and eutigoside-A
  作者：Duc Thinh Khong、Zaher M.A. Judeh

  DOI：10.1016/j.tetlet.2016.11.116

  日期：2017.1

  convenient 4-step synthesis of calceolarioside-B 1 and eutigoside-A 2 in high overall yield is described. The key step involved the regioselective, Me2SnCl2-catalyzed O-6 acylation of unprotected 2-phenylethyl-β-d-glucosides 5a–b with cinnamoyl chlorides 6a–b in excellent yields. Acylation at O-6 is selective with the acid chlorides used. This work serves as a model for the convenient synthesis of phenylpropanoid

  描述了以高的总收率方便地进行四步合成钙黄绿藻糖苷-B 1和洋红甙-A 2的方法。关键步骤涉及使用未反应的2-苯基乙基-β- d-葡萄糖苷5a – b与肉桂酰氯6a – b的区域选择性，Me 2 SnCl 2催化的O -6酰化，产率极高。在O -6的酰化作用对所用的酰氯是选择性的。这项工作为方便合成在O -6上酰化的苯丙烷类糖苷提供了模型。