6-deoxy-1,2:3,5-di-O-isopropylidene-6-thio-α-D-glucofuranose | 133692-60-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-deoxy-1,2:3,5-di-O-isopropylidene-6-thio-α-D-glucofuranose
• 英文别名: [(1S,2R,6R,8S,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[6.4.0.02,6]dodecan-9-yl]methanethiol
• CAS: 133692-60-1
• 化学式: C₁₂H₂₀O₅S
• 分子量: 276.354
• InChiKey: OBARUAFHZNTKRT-HOTMZDKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-deoxy-1,2:3,5-di-O-isopropylidene-6-thio-α-D-glucofuranose 在 盐酸 、 对甲苯磺酸 作用下， 以 水 、 丙酮 为溶剂， 反应 1.0h， 生成 2,3,5-tri-O-acetyl-1,6-dideoxy-1,6-epithio-β-D-glucofuranose
  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：

  1,2:3,5-bis-O-(1-methylethylidene)-6-(p-tolylsulfonyl)-α-D-glucofuranose 在 sodium tetrahydroborate 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.25h， 生成 6-deoxy-1,2:3,5-di-O-isopropylidene-6-thio-α-D-glucofuranose
  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

• Ohle; Mertens, Chemische Berichte, 1935, vol. 68, p. 2176,2186
  作者：Ohle、Mertens

  DOI：——

  日期：——
• WO2023/92188
  申请人：——

  公开号：——

  公开（公告）日：——