1,2-O:5,6-O,S-diisopropylidene-3-O-methanesulfonyl-6-thio-β-L-idofuranose | 288850-16-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: 1,2-O:5,6-O,S-diisopropylidene-3-O-methanesulfonyl-6-thio-β-L-idofuranose
• 英文别名: [(3aR,5R,6S,6aR)-5-[(5R)-2,2-dimethyl-1,3-oxathiolan-5-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] methanesulfonate
• CAS: 288850-16-8
• 化学式: C₁₃H₂₂O₇S₂
• 分子量: 354.445
• InChiKey: BFCDDMCZTGKAPZ-OGBGREFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,2-O:5,6-O,S-diisopropylidene-3-O-methanesulfonyl-6-thio-β-L-idofuranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以72%的产率得到1,2-O:5,6-O,S-diisopropylidene-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
• 作为产物：
  描述：

  3,6-anhydro-1,2-O-isopropylidene-3-O-metahnesulphonyl-β-L-idofuranose 在 sodium tetrahydroborate 、 sodium methylate 、 对甲苯磺酸 作用下， 以 吡啶 、 甲醇 、 丙酮 为溶剂， 反应 2.75h， 生成 1,2-O:5,6-O,S-diisopropylidene-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.