6-thio-β-D-fructopyranose | 56578-20-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: 6-thio-β-D-fructopyranose
• 英文别名: β-D-6-thio-fructopyranose；6-Thio-I(2)-D-fructopyranose；(2R,3S,4R,5S)-2-(hydroxymethyl)thiane-2,3,4,5-tetrol
• CAS: 56578-20-2
• 化学式: C₆H₁₂O₅S
• 分子量: 196.224
• InChiKey: VFFBXSDNDMWYPS-ARQDHWQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 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

• 作为反应物：
  描述：

  6-thio-β-D-fructopyranose 、 乙酸酐 在 zinc(II) chloride 作用下， 生成 Acetic acid (1S,2S)-2,4-diacetoxy-1-((S)-1-acetoxy-2-acetylsulfanyl-ethyl)-3-oxo-butyl ester
  参考文献：
  名称：

  6-thio-β-D-fructopyranose

  摘要：

  DOI：

  10.1016/s0008-6215(00)83165-1
• 作为产物：
  描述：

  [(2S,3S,4S,5S)-2-(acetylsulfanylmethyl)-4,5-dihydroxy-5-(hydroxymethyl)oxolan-3-yl] acetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 6-thio-β-D-fructopyranose
  参考文献：
  名称：

  The First Chemical Synthesis of 6-Thio-D-fructopyranose via Methyl 6-Bromo-6-deoxy-1,3-O-isopropylidene-α-D-fructofuranoside as a Key Intermediate

  摘要：

  Selective bromination of sucrose, followed by acetalation with 2,2-dimethoxypropane in 1,4-dioxane in the presence of p-toluenesulfonic acid, afforded methyl 6-bromo-6-deoxy-1,3-O-isopropylidene-alpha-D-fructofuranoside (4). The first chemical synthesis of 6-thio-D-fructopyranose was accomplished from 4 through its 6-S-acetyl-6-thio derivative.

  DOI：

  10.3987/com-06-10965

文献信息

• A New Route to Deoxythio sugars Based on Aldolases
  作者：Wen-Chih Chou、Lihren Chen、Jim-Min Fang、Chi-Huey Wong

  DOI：10.1021/ja00093a018

  日期：1994.7

  A new route to deoxythiosugars based on aldolases has been developed. Representative syntheses of several thioketoses and 1-deoxy-5-thio-D-glucose, 1-deoxy-5-thio-D-galactose, 1-deoxy-5-thio-L-altrose, 1-deoxy-5-thio-D-mannose, 1-deoxy-5-thio-L-mannose, and 2-deoxy-5-thio-D-ribose are illustrated with the use of fructose 1,6-diphosphate aldolase, fuculose 1-phosphate aldolase, rhamnulose 1-phosphate aldolase, and 2-deoxyribose 5-phosphate aldolase in reaction with an appropriate thioaldehyde, followed by reduction with triethylsilane in the presence of BF3.Et(2)O.