Thioacetic acid S-[(2R,3R,4S)-3,4-bis-benzyloxy-5-(2-oxo-ethyl)-tetrahydro-furan-2-ylmethyl] ester | 592532-90-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Thioacetic acid S-[(2R,3R,4S)-3,4-bis-benzyloxy-5-(2-oxo-ethyl)-tetrahydro-furan-2-ylmethyl] ester
• CAS: 592532-90-6
• 化学式: C₂₃H₂₆O₅S
• 分子量: 414.522
• InChiKey: HCWXNCLIVKDIIQ-KVROEHFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  29.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Thioacetic acid S-[(2R,3R,4S)-3,4-bis-benzyloxy-5-(2-oxo-ethyl)-tetrahydro-furan-2-ylmethyl] ester 在 sodium methylate 作用下， 以76%的产率得到((2S,3R,4S,5R)-3,4-Bis-benzyloxy-5-hydroxy-tetrahydro-thiopyran-2-yl)-acetaldehyde
  参考文献：
  名称：

  Synthesis of thio-C-glycosides from 2′-carbonylalkyl C-glycosides by a tandem β-elimination and intramolecular hetero-Michael addition

  摘要：

  2'-Carbonyl 5-S-acetyl-C-glycofuranosides and 2'-carbonyl 4-S-acetyl-C-glycopyranosides were converted in good yields to respective 5-thio-C-glycopyranosides and 4-thio-C-glycofuranosides under base treatment. The transformation was resulted from beta-elimination on 2'-carbonyl C-glycoside to form alpha,beta-conjugated aldehyde (or ketone) and following intramolecular hetero-Michael addition by the thiol group. Crown Copyright (C) 2003 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01039-6
• 作为产物：
  描述：

  Thioacetic acid S-((2R,3R,4S)-5-allyl-3,4-bis-benzyloxy-tetrahydro-furan-2-ylmethyl) ester 在 臭氧 、 锌 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 1.0h， 以67%的产率得到Thioacetic acid S-[(2R,3R,4S)-3,4-bis-benzyloxy-5-(2-oxo-ethyl)-tetrahydro-furan-2-ylmethyl] ester
  参考文献：
  名称：

  Synthesis of thio-C-glycosides from 2′-carbonylalkyl C-glycosides by a tandem β-elimination and intramolecular hetero-Michael addition

  摘要：

  2'-Carbonyl 5-S-acetyl-C-glycofuranosides and 2'-carbonyl 4-S-acetyl-C-glycopyranosides were converted in good yields to respective 5-thio-C-glycopyranosides and 4-thio-C-glycofuranosides under base treatment. The transformation was resulted from beta-elimination on 2'-carbonyl C-glycoside to form alpha,beta-conjugated aldehyde (or ketone) and following intramolecular hetero-Michael addition by the thiol group. Crown Copyright (C) 2003 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01039-6