5-thio-β-D-galactopyranose | 1447970-68-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: 5-thio-β-D-galactopyranose
• 英文别名: (2R,3R,4S,5R,6R)-6-(hydroxymethyl)thiane-2,3,4,5-tetrol
• CAS: 1447970-68-4
• 化学式: C₆H₁₂O₅S
• 分子量: 196.224
• InChiKey: KNWYARBAEIMVMZ-FPRJBGLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  126
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6-O-acetyl-5-S-acetyl-1,2-O-isopropylidene-3-O-methylsulfonyl-5-thio-α-D-galactofuranose 在 camphor-10-sulfonic acid 、 水 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 36.0h， 生成 5-thio-α-D-galactopyranose 、 5-thio-β-D-galactopyranose
  参考文献：
  名称：

  Synthesis of 5-Thio-D- Galactopyranose

  摘要：

  5-Thio-D-galactopyranose has been synthesized from diacetone galactofuranose in nine steps and 13.4% overall yield. The key step involved a successful conversion of furanosyl 5,6-epoxide with an L-altrose configuration into the corresponding 5,6-thiirane D-galactose derivative, which was hydrolyzed to the target compound.

  DOI：

  10.1080/07328303.2013.800086

文献信息

• Crystalline sugar compositions and method of making
  申请人：Major Michael

  公开号：US20060293250A1

  公开（公告）日：2006-12-28

  Described are novel crystalline pivaloyl furanoses and methods of crystallizing the pivaloyl furanoses. These compounds are useful as intermediates in the synthesis of compounds such as the deoxyjirimycins and nojirimycins and are particularly useful as intermediates for production on a multi-kg scale. Particular crystalline compounds include 1,2,3,6-tetrapivaloyl-α-D-galactofuranose, 1,2,3,6-tetrapivaloyl-α-L-altrofuranose, and 5-azido-5-deoxy-1,2,3,6-tetrapivaloyl-α-D-galactofuranose.

  本文描述了新型结晶式戊酰基呋喃糖以及结晶戊酰基呋喃糖的方法。这些化合物可用作合成脱氧吉利霉素和诺吉霉素等化合物的中间体，并且在多千克级别的生产中特别有用。特定的结晶化合物包括1,2,3,6-四戊酰基-α-D-半乳糖呋喃糖、1,2,3,6-四戊酰基-α-L-阿尔卓糖呋喃糖和5-叠氮基-5-脱氧-1,2,3,6-四戊酰基-α-D-半乳糖呋喃糖。
• CRYSTALLINE SUGAR COMPOSITIONS AND METHOD OF MAKING
  申请人：Amicus Therapeutics, Inc.

  公开号：EP1888612A1

  公开（公告）日：2008-02-20
• [EN] CRYSTALLINE SUGAR COMPOSITIONS AND METHOD OF MAKING<br/>[FR] COMPOSITIONS DE SUCRE CRISTALLIN ET PROCEDE DE PRODUCTION ASSOCIE
  申请人：AMICUS THERAPEUTICS INC

  公开号：WO2006133447A1

  公开（公告）日：2006-12-14

  [EN] Described are novel crystalline pivaloyl furanoses and methods of crystallizing the pivaloyl furanoses. These compounds are useful as intermediates in the synthesis of compounds such as the deoxyjirimycins and nojirimycins and are particularly useful as intermediates for production on a multi-kg scale. Particular crystalline compounds include 1,2,3,6-tetrapivaloyl-a-D-galactofuranose, 1,2,3,6- tetrapivaloyl-a-L-altrofuranose, and 5-azido-5-deoxy-l,2,3,6-tetrapivaloyl-a-D- galactofuranose.
  [FR] L'invention concerne des nouveaux furanoses de pivaloyle et des procédés de cristallisation de ceux-ci. Ces composés sont utiles en tant qu'intermédiaires dans la synthèse de composés de type déoxyjirimycines et nojirimycines et sont particulièrement utiles en tant qu'intermédiaires pour une production à une échelle multi-kg. A titre de composés cristallins particuliers, on peut citer le 1,2,3,6-tétrapivaloyl-a-D-galactofuranose ; le 1,2,3,6-tétrapivaloyl-a-L-altrofuranose, et le 5-azido-5-déoxy-l,2,3,6-tétrapivaloyl-a-D-galactofuranose.
• Synthesis of 5-Thio-D- Galactopyranose
  作者：Yuancheng Wang、Yuguo Du

  DOI：10.1080/07328303.2013.800086

  日期：2013.5.4

  5-Thio-D-galactopyranose has been synthesized from diacetone galactofuranose in nine steps and 13.4% overall yield. The key step involved a successful conversion of furanosyl 5,6-epoxide with an L-altrose configuration into the corresponding 5,6-thiirane D-galactose derivative, which was hydrolyzed to the target compound.