Methyl 2-acetamido-4,6-di-O-acetyl-3-S-acetyl-2-desoxy-3-thio-α-D-mannopyranosid | 82161-33-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 2-acetamido-4,6-di-O-acetyl-3-S-acetyl-2-desoxy-3-thio-α-D-mannopyranosid
• 英文别名: methyl-2-acetamido-4,6-di-O-acetyl-3-S-acetyl-2-deoxy-3-thio-α-D-mannopyranoside；[(2R,3R,4R,5R,6S)-5-acetamido-3-acetyloxy-4-acetylsulfanyl-6-methoxyoxan-2-yl]methyl acetate
• CAS: 82161-33-9
• 化学式: C₁₅H₂₃NO₈S
• 分子量: 377.416
• InChiKey: DXEAKQVFQJAXAB-KHMAMNHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  143
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  methyl 2-amino-4,6-O-benzylidene-2-deoxy-2-N-<(methylthio)thiocarbonyl>-α-D-altropyranoside 在 aluminum amalgam 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 吡啶 为溶剂， 反应 111.0h， 生成 Methyl 2-acetamido-4,6-di-O-acetyl-3-S-acetyl-2-desoxy-3-thio-α-D-mannopyranosid
  参考文献：
  名称：

  Synthesis of Methyl 2-Acetamido-4,6-di-O-acetyl-3-S-acetyl-2-deoxy-3-thio-?-D-mannopyranoside

  摘要：

  AbstractMethyl‐2‐acetamido‐4,6‐di‐O‐acetyl‐3‐S‐acetyl‐2‐deoxy‐3‐thio‐α‐D‐mannopy‐ranoside has been synthesized by conversion of methyl 2‐amino‐2‐deoxy‐4,6‐O‐benzylidene‐α‐D‐altropyranoside into the corresponding 3‐O‐methanesulfony1‐2‐N‐[(methylthio)thiocarbonyl]derivative followed by intramolecular displacement of the 3‐O‐methanesulfonyloxy group with the (methylthio)thiocarbamoyl group.

  DOI：

  10.1002/hlca.19820650205

文献信息

• The thiazoline ring as a protective group of 2-amino-2- deoxy-3-thio-mannose
  作者：R. Brossmer、H. Mack

  DOI：10.1016/0040-4039(81)89012-0

  日期：1981.1

  A new synthesis of 2-amino-2-deoxy-3-thio-mannose is described, in which both the amino and the thio functions are protected in form of a thiazoline ring.

  描述了2-氨基-2-脱氧-3-硫代甘露糖的新合成，其中氨基和硫代官能团均以噻唑啉环的形式被保护。
• Synthese von 6-thiosialinsäuren
  作者：Hans Mack、Reinhard Brossmer

  DOI：10.1016/s0040-4020(98)00167-7

  日期：1998.4

  The synthesis of 2-acetamido-2-deoxy-3-thio-D-mannose (11) is described. Chain elongation of thiazoline 10 with potassium-di-O-tbutyl-oxaloacetate yields epimeric 6-thiosialic acids 14 and 15. Chain extension of 18 with oxaloacetate/Ni++ results in the formation of N-acetyl-6-thioneuraminic acid (21). Starting from 21 synthesis of alpha-azide 25 and dehydro-compound 27 was accomplished by treatment of 23 with sodium azide. On the other hand lewis acid catalyzed azidation of 22 beta with azidotrimethylsilane afforded beta-azide 29. (C) 1998 Elsevier Science Ltd. All rights reserved.