methyl 4-S-acetyl-2,3,6-tri-O-benzoyl-4-thio-α-D-galactopyranoside | 118868-79-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-S-acetyl-2,3,6-tri-O-benzoyl-4-thio-α-D-galactopyranoside
• 英文别名: methyl 4-S-acetyl-2,3,6-tri-O-benzoyl-α-D-galactopyranoside；[(2R,3S,4R,5R,6S)-3-acetylsulfanyl-4,5-dibenzoyloxy-6-methoxyoxan-2-yl]methyl benzoate
• CAS: 118868-79-4
• 化学式: C₃₀H₂₈O₉S
• 分子量: 564.613
• InChiKey: CEXAWRRTCKMJBU-BFDLQSRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 4-S-acetyl-2,3,6-tri-O-benzoyl-4-thio-α-D-galactopyranoside 在 一水合肼 、 三(2-羰基乙基)磷盐酸盐 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.07h， 以84%的产率得到methyl 2,3,6-tri-O-benzoyl-4-deoxy-α-D-xylo-hexopyranoside
  参考文献：
  名称：

  A One-Pot Method for Removal of Thioacetyl Group via Desulfurization under Ultraviolet Light To Synthesize Deoxyglycosides

  摘要：

  We herein developed an efficient method for removing thioacetyl to synthesize acylated deoxy glycosides in a one-pot reaction, where the thioacetyl was selectively deacetylated by hydrazine hydrate in DMF within 2-5 min at room temperature, followed by desulfurization under UV light for 1-2 h in the presence of TCEP center dot HCl. The method was then used to synthesize 2-deoxy glycosides with absolute alpha/beta-configuration via stereoselective control of C-2 thioacetate in glycosylation.

  DOI：

  10.1021/acs.orglett.9b02033
• 作为产物：
  描述：

  methyl 2,3,6-tri-O-benzoyl-α-D-glucopyranoside 在 吡啶 、 potassium thioacyanate 、 溶剂黄146 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 83.0h， 生成 methyl 4-S-acetyl-2,3,6-tri-O-benzoyl-4-thio-α-D-galactopyranoside
  参考文献：
  名称：

  A convenient synthesis of 4-thio-D-galactofuranose

  摘要：

  DOI：

  10.1021/jo00269a025

文献信息

• VARELA, OSCAR;CICERO, DANIEL;DE, LEDERKREMER ROSA M., J. ORG. CHEM., 54,(1989) N, C. 1884-1890
  作者：VARELA, OSCAR、CICERO, DANIEL、DE, LEDERKREMER ROSA M.

  DOI：——

  日期：——
• A One-Pot Method for Removal of Thioacetyl Group via Desulfurization under Ultraviolet Light To Synthesize Deoxyglycosides
  作者：Jian-Tao Ge、Lang Zhou、Tao Luo、Jian Lv、Hai Dong

  DOI：10.1021/acs.orglett.9b02033

  日期：2019.8.2

  We herein developed an efficient method for removing thioacetyl to synthesize acylated deoxy glycosides in a one-pot reaction, where the thioacetyl was selectively deacetylated by hydrazine hydrate in DMF within 2-5 min at room temperature, followed by desulfurization under UV light for 1-2 h in the presence of TCEP center dot HCl. The method was then used to synthesize 2-deoxy glycosides with absolute alpha/beta-configuration via stereoselective control of C-2 thioacetate in glycosylation.
• A convenient synthesis of 4-thio-D-galactofuranose
  作者：Oscar Varela、Daniel Cicero、Rosa M. De Lederkremer

  DOI：10.1021/jo00269a025

  日期：1989.4