2,3,4-tri-O-pivaloyl-α-L-rhamnopyranosyl trichloroacetimidate | 335591-67-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-pivaloyl-α-L-rhamnopyranosyl trichloroacetimidate
• 英文别名: 2,3,4-tri-O-pivaloyl-L-rhamnopyranosyl trichloroacetimidate；pivaloyl(-2)[pivaloyl(-3)][pivaloyl(-4)]Rha(a)-O-C(NH)CCl3；[(2S,3S,4R,5R,6S)-4,5-bis(2,2-dimethylpropanoyloxy)-2-methyl-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] 2,2-dimethylpropanoate
• CAS: 335591-67-8
• 化学式: C₂₃H₃₆Cl₃NO₈
• 分子量: 560.9
• InChiKey: MYOOEDXJKZNKDC-AHDPXTMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-pivaloyl-α-L-rhamnopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 [(2S,3S,4R,5R,6R)-6-[(2E)-2-(1-benzyl-3-oxoindol-2-ylidene)-3-oxoindol-1-yl]-4,5-bis(2,2-dimethylpropanoyloxy)-2-methyloxan-3-yl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  First Synthesis ofN-Indigoglycosides - Analogues of Cancerostatic Akashines

  摘要：

  基于 N-苄基靛蓝与三-O-pivaloyl-δ-l-rhamnosyl trichloroacetimidate 的糖基化，以及随后 O- 与 N-糖苷的重排，首次完成了 N-靛基糖苷的简单合成。N-Indigoglycosides 具有重要的药理作用，并存在于抗癌天然碱中。

  DOI：

  10.1055/s-2005-918489
• 作为产物：
  描述：

  1,2,3,4-tetra-O-pivaloyl-α/β-L-rhamnopyranoside 在 氢溴酸 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 35.0h， 生成 2,3,4-tri-O-pivaloyl-α-L-rhamnopyranosyl trichloroacetimidate
  参考文献：
  名称：

  An improved synthesis of the saponin, polyphyllin D

  摘要：

  Polyphyllin D, namely diosgenyl alpha -L-rhamnopyranosyl-(1->2)-[(alpha -L-arabinofuranosyl)-(1->4)]-beta -D-glucopyranoside, was synthesized from diosgenyl-beta -D-glucopyranoside in four steps and in 30% overall yield, taking advantage of regioselective pivaloylation and alpha -L-rhamnopyranosylation reactions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00014-3

文献信息

• Synthesis of solanum glycosides
  申请人：——

  公开号：US20040259814A1

  公开（公告）日：2004-12-23

  The present invention relates to the chemical synthesis of solanum glycosides, in particular to the synthesis of solamargine as well as to novel &bgr;-monosaccharide Intermediate compounds.

  本发明涉及茄碱苷的化学合成，特别是茄碱苷以及新型&bgr;-单糖中间体化合物的合成。
• Facile Conversion of Spirostan Saponin into Furostan Saponin:  Synthesis of Methyl Protodioscin and Its 26-Thio-analogue
  作者：Ming Li、Biao Yu

  DOI：10.1021/ol060594w

  日期：2006.6.1

  A facile approach for the conversion of a spirostan saponin into its furostan counterpart, as illustrated by the transformation of dioscin to methyl protodioscin (and its 26-thio-analogue), has been developed.
• CHEMICAL SYNTHESIS OF SOLAMARGINE
  申请人：GlycoMed Sciences Limited

  公开号：EP1421100A1

  公开（公告）日：2004-05-26
• [EN] SYNTHESIS OF SOLANUM GLYCOSIDES<br/>[FR] SYNTHESE CHIMIQUE DE SOLAMARGINE
  申请人：GLYCOMED SCIENCES LTD

  公开号：WO2003018604A1

  公开（公告）日：2003-03-06

  The present invention relates to the chemical synthesis of solanum glycosides, in particular to the synthesis of solamargine as well as to novel β-monosaccharide intermediate compounds.
• An improved synthesis of the saponin, polyphyllin D
  作者：Bing Li、Biao Yu*、Yongzheng Hui*、Ming Li、Xiuwen Han、Kwok-Pui Fung

  DOI：10.1016/s0008-6215(01)00014-3

  日期：2001.3

  Polyphyllin D, namely diosgenyl alpha -L-rhamnopyranosyl-(1->2)-[(alpha -L-arabinofuranosyl)-(1->4)]-beta -D-glucopyranoside, was synthesized from diosgenyl-beta -D-glucopyranoside in four steps and in 30% overall yield, taking advantage of regioselective pivaloylation and alpha -L-rhamnopyranosylation reactions. (C) 2001 Elsevier Science Ltd. All rights reserved.