methyl 6-S-acetyl-2,3,4-tri-O-benzoyl-α-D-glucopyranoside | 686341-62-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-S-acetyl-2,3,4-tri-O-benzoyl-α-D-glucopyranoside
• CAS: 686341-62-8
• 化学式: C₃₀H₂₈O₉S
• 分子量: 564.613
• InChiKey: CZYKOZGTDWDEME-UKGKTARGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.31
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  114.43
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  methyl 6-S-acetyl-2,3,4-tri-O-benzoyl-α-D-glucopyranoside 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82%的产率得到methyl 2,3,4-tri-O-benzoyl-6-deoxy-α-D-glucopyranoside
  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：

  甲基2,3,4-三-O-苯甲酰-α-D-吡喃葡萄糖苷 、 硫代乙酸 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 以67%的产率得到methyl 6-S-acetyl-2,3,4-tri-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  Rhenium(V)-Catalyzed Synthesis of 2-Deoxy-α-glycosides

  摘要：

  A mild method for the synthesis of 2-deoxysugars from the coupling of glycals with a range of nucleophiles is described. The method employs 1 mol % of an air- and moisture-tolerant rhenium-oxo complex [ReOCl3(SMe2)(Ph3PO)] as a catalyst for the formation of O-, N-, and S-alpha-glycosides. The catalytic system tolerates a number of commonly employed protecting groups, including isopropylidene acetals, alkyl and silyl ethers, acetates, and benzoates. Furthermore, the high-oxidation-state complex selectively catalyzes the coupling with the glycal acceptor in preference to oxidation of the glycals, alcohols, and even thiols.

  DOI：

  10.1021/ja031895t