6-S-acetyl-1,2-O-isopropylidene-3-O-methanesulfonyl-6-thio-β-L-idofuranose | 288850-15-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-S-acetyl-1,2-O-isopropylidene-3-O-methanesulfonyl-6-thio-β-L-idofuranose
• 英文别名: S-[(2R)-2-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-methylsulfonyloxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl] ethanethioate
• CAS: 288850-15-7
• 化学式: C₁₂H₂₀O₈S₂
• 分子量: 356.418
• InChiKey: GLDATOFFPLEDFE-OGBGREFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6-S-acetyl-1,2-O-isopropylidene-3-O-methanesulfonyl-6-thio-β-L-idofuranose 在 sodium tetrahydroborate 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.75h， 生成 Methanesulfonic acid (3aR,5R,6S,6aR)-5-((R)-1-hydroxy-2-mercapto-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
  参考文献：
  名称：

  Action of acid on 6-thio-hexose derivatives. Synthesis of 1,6-epithio-hexofuranoses

  摘要：

  Reaction of 5,6-anhydro-1,2-O-isopropylidene-3-O-methanesulfonyl-beta-L-idofuranose with thioacetic acid in pyridine gave 6-S-acetyl-1,2-O-isopropylidene-3-O-methanesulfonyl-6-thio-beta-L-idofuranose, which was deacetylated and the resultant thiol was converted into 1,2-O:5,6-O,S-diisopropylidene-3-O-methanesulfonyl-beta-L-idofuranose. Alkaline cleavage of the mesyl group gave 1,2-O: 5,6-O,S-diisopropylidene-X-L-idofuranose which on treatment with hot dilute hydrochloric acid gave, after acetylation, 2,3,5-tri-O-acetyl-1,6-dideoxy-1,6-epithio-alpha-L-idofuranose and not the expected idopyranose isomer. 1,2: 3,5-Di-O-isopropylidene-6-O-toluene-p-sulfonyl-alpha-D-glucofuranose was converted into 6-S-acetyl-1,2:3,5-di-O-isopropylidene-6-thio-alpha-D-glucofuranose; conversion into the 6-thiol and isomerisation in acidified acetone gave 1,2-O:5,6-O,S-diisopropylidene-6-thio-alpha-D-glucofuranose. Acid treatment of this diacetal, or the isomeric 1,2:3,5-di-O-isopropylidene-6-thio-alpha-D-glucofuranose, followed by acetylation gave 2,3,5-tri-O-acetyl-1,6-dideoxy-1,6-epithio-beta-D-glucofuranose. Similar treatment of 1,2:3,4-di-O-isopropylidene-6-thio-alpha-D-galactopyranose gave 2,3,5-tri-O-acetyl-1,6-dideoxy-1,6-epithio-alpha-D-galactofuranose. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00028-8
• 作为产物：
  描述：

  3,6-anhydro-1,2-O-isopropylidene-3-O-metahnesulphonyl-β-L-idofuranose 、 硫代乙酸 以 吡啶 为溶剂， 反应 1.0h， 以75%的产率得到6-S-acetyl-1,2-O-isopropylidene-3-O-methanesulfonyl-6-thio-β-L-idofuranose
  参考文献：
  名称：

  Action of acid on 6-thio-hexose derivatives. Synthesis of 1,6-epithio-hexofuranoses

  摘要：

  Reaction of 5,6-anhydro-1,2-O-isopropylidene-3-O-methanesulfonyl-beta-L-idofuranose with thioacetic acid in pyridine gave 6-S-acetyl-1,2-O-isopropylidene-3-O-methanesulfonyl-6-thio-beta-L-idofuranose, which was deacetylated and the resultant thiol was converted into 1,2-O:5,6-O,S-diisopropylidene-3-O-methanesulfonyl-beta-L-idofuranose. Alkaline cleavage of the mesyl group gave 1,2-O: 5,6-O,S-diisopropylidene-X-L-idofuranose which on treatment with hot dilute hydrochloric acid gave, after acetylation, 2,3,5-tri-O-acetyl-1,6-dideoxy-1,6-epithio-alpha-L-idofuranose and not the expected idopyranose isomer. 1,2: 3,5-Di-O-isopropylidene-6-O-toluene-p-sulfonyl-alpha-D-glucofuranose was converted into 6-S-acetyl-1,2:3,5-di-O-isopropylidene-6-thio-alpha-D-glucofuranose; conversion into the 6-thiol and isomerisation in acidified acetone gave 1,2-O:5,6-O,S-diisopropylidene-6-thio-alpha-D-glucofuranose. Acid treatment of this diacetal, or the isomeric 1,2:3,5-di-O-isopropylidene-6-thio-alpha-D-glucofuranose, followed by acetylation gave 2,3,5-tri-O-acetyl-1,6-dideoxy-1,6-epithio-beta-D-glucofuranose. Similar treatment of 1,2:3,4-di-O-isopropylidene-6-thio-alpha-D-galactopyranose gave 2,3,5-tri-O-acetyl-1,6-dideoxy-1,6-epithio-alpha-D-galactofuranose. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00028-8

文献信息

• Action of acid on 6-thio-hexose derivatives. Synthesis of 1,6-epithio-hexofuranoses
  作者：Neil A. Hughes、Nigel D. Todhunter

  DOI：10.1016/s0008-6215(00)00028-8

  日期：2000.6

  Reaction of 5,6-anhydro-1,2-O-isopropylidene-3-O-methanesulfonyl-beta-L-idofuranose with thioacetic acid in pyridine gave 6-S-acetyl-1,2-O-isopropylidene-3-O-methanesulfonyl-6-thio-beta-L-idofuranose, which was deacetylated and the resultant thiol was converted into 1,2-O:5,6-O,S-diisopropylidene-3-O-methanesulfonyl-beta-L-idofuranose. Alkaline cleavage of the mesyl group gave 1,2-O: 5,6-O,S-diisopropylidene-X-L-idofuranose which on treatment with hot dilute hydrochloric acid gave, after acetylation, 2,3,5-tri-O-acetyl-1,6-dideoxy-1,6-epithio-alpha-L-idofuranose and not the expected idopyranose isomer. 1,2: 3,5-Di-O-isopropylidene-6-O-toluene-p-sulfonyl-alpha-D-glucofuranose was converted into 6-S-acetyl-1,2:3,5-di-O-isopropylidene-6-thio-alpha-D-glucofuranose; conversion into the 6-thiol and isomerisation in acidified acetone gave 1,2-O:5,6-O,S-diisopropylidene-6-thio-alpha-D-glucofuranose. Acid treatment of this diacetal, or the isomeric 1,2:3,5-di-O-isopropylidene-6-thio-alpha-D-glucofuranose, followed by acetylation gave 2,3,5-tri-O-acetyl-1,6-dideoxy-1,6-epithio-beta-D-glucofuranose. Similar treatment of 1,2:3,4-di-O-isopropylidene-6-thio-alpha-D-galactopyranose gave 2,3,5-tri-O-acetyl-1,6-dideoxy-1,6-epithio-alpha-D-galactofuranose. (C) 2000 Elsevier Science Ltd. All rights reserved.