2-(2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyl)-N,N-(pentamethylene)ethanethioamide | 207276-62-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyl)-N,N-(pentamethylene)ethanethioamide
• 英文别名: 2,3:5,6-di-O-isopropylidene-1-(piperidin-1-ylthiocarbonylmethyl)-β-D-mannofuranose；2-[(3aS,4R,6S,6aR)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-1-piperidin-1-ylethanethione
• CAS: 207276-62-8
• 化学式: C₁₉H₃₁NO₅S
• 分子量: 385.525
• InChiKey: JGSGRFMQEKAWOW-CNLQAYEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  81.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyl)-N,N-(pentamethylene)ethanethioamide 在 三氟乙酸 作用下， 以 乙醚 、 水 为溶剂， 反应 24.0h， 以98%的产率得到N-[2-C-(2,3:5,6-tetrahydroxy)-β-D-mannofuranosylethanethioyl]piperidine
  参考文献：
  名称：

  合成新的2-C-（2,3：5,6-二-O-异亚丙基）-β-D-呋喃呋喃糖基二硫代乙酸酯衍生物。

  摘要：

  通过2-C-呋喃呋喃糖基二硫代乙酸酯通过不同胺的硫酰化反应已经合成了各种新的C-糖苷。氨基酸，二胺和多胺（普雷斯汀，亚精胺，亚精胺）和一种氨基醇特别用于产生糖硫肽或“博拉”结构的前体。

  DOI：

  10.1016/j.carres.2004.12.025
• 作为产物：
  描述：

  哌啶 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 反应 28.0h， 生成 2-(2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyl)-N,N-(pentamethylene)ethanethioamide
  参考文献：
  名称：

  Synthesis of d -mannofuranosyl-ethanethioamides and the corresponding ethanedithioate, the first C -glycosyl derivative with thioacylating properties

  摘要：

  D-Mannofuranosyl-ethanethioamides were prepared in gold yields via a Homer-Wadsworth-Emmons reaction of thiocarbamoylmethylphosphonates with 2,3:5,6-di-O-isopropylidene-alpha-D-mannofuranose. New glycosyl-ethanethioamides were obtained and one of them was converted into the corresponding dithioester which is a potential sugar substituted thioacylating agent for aminoacids. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00304-9

文献信息

• 2-(2,3:5,6-Di-<i>O</i>-isopropylidene-β-<scp>D</scp>-mannofuranosyl)-<i>N</i>,<i>N</i>-(pentamethylene)ethanethioamide
  作者：P. Marchand、S. Masson、D. Rachinel、J.-F. Saint-Clair、M.-T. Averbuch-Pouchot

  DOI：10.1107/s0108270199006459

  日期：1999.9.15

  The title compound, C19H31NO5S, was prepared using a Wittig-Horner olefination followed by an intramolecular Michael addition. Two diastereoisomers were obtained in a 80:20 (beta:alpha) ratio. The stereochemistry of the major anomer (beta, thermodynamic) was based on NMR (C-13 and H-1) spectra. The present X-ray structure determination confirms the configuration of this product.
• Synthesis of d -mannofuranosyl-ethanethioamides and the corresponding ethanedithioate, the first C -glycosyl derivative with thioacylating properties
  作者：Franck Sandrinelli、Sylvie Le Roy-Gourvennec、Serge Masson、Patrick Rollin

  DOI：10.1016/s0040-4039(98)00304-9

  日期：1998.4

  D-Mannofuranosyl-ethanethioamides were prepared in gold yields via a Homer-Wadsworth-Emmons reaction of thiocarbamoylmethylphosphonates with 2,3:5,6-di-O-isopropylidene-alpha-D-mannofuranose. New glycosyl-ethanethioamides were obtained and one of them was converted into the corresponding dithioester which is a potential sugar substituted thioacylating agent for aminoacids. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• Synthesis of new 2-C-(2,3:5,6-di-O-isopropylidene)-β-d-mannofuranosyldithioacetate derivatives
  作者：Zaira J. Dominguez、Patrice Marchand、Mihaela Gulea、Serge Masson

  DOI：10.1016/j.carres.2004.12.025

  日期：2005.3

  Various new C-glycosides have been synthesized through the thioacylation reaction of different amines by a 2-C-mannofuranosyldithioacetate. Amino acids, di- and polyamines (putresceine, spermine, spermidine) and one amino alcohol were in particular used to generate glycothiopeptidic or precursors of "bola" structures.

  通过2-C-呋喃呋喃糖基二硫代乙酸酯通过不同胺的硫酰化反应已经合成了各种新的C-糖苷。氨基酸，二胺和多胺（普雷斯汀，亚精胺，亚精胺）和一种氨基醇特别用于产生糖硫肽或“博拉”结构的前体。