Acetic acid (2R,3R,4S,5R)-3,5-diacetoxy-2-bromo-tetrahydro-thiopyran-4-yl ester | 155487-89-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (2R,3R,4S,5R)-3,5-diacetoxy-2-bromo-tetrahydro-thiopyran-4-yl ester
• 英文别名: [(3R,4S,5R,6R)-4,5-diacetyloxy-6-bromothian-3-yl] acetate
• CAS: 155487-89-1
• 化学式: C₁₁H₁₅BrO₆S
• 分子量: 355.207
• InChiKey: MWYPHOWMKHNMBH-MMWGEVLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5R)-3,5-diacetoxy-2-bromo-tetrahydro-thiopyran-4-yl ester 在 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 2.0h， 生成 4-cyanophenyl 1,5-dithio-α-L-arabinopyranoside
  参考文献：
  名称：

  Synthesis of 4-cyanophenyl and 4-nitrophenyl 1,5-dithio-l- and -d-arabinopyranosides possessing antithrombotic activity1Orally active antithrombotic thioglycosides, Part VI. For Part V, see[1].12Presented partly at the XVIIIth International Carbohydrate Symposium, Milan, 21–26 July 1996. Abstr. BP092.2

  摘要：

  5-S-Benzoyl-2,3-O-isopropylidene-5-thio-L-arabinose, prepared from L-arabinose diethyl dithioacetal gave, on treatment with sodium methoxide in methanol, 4-O-benzoyl-2,3-O-isopropylidene-5-thio-L-arabinopyranose 12 which was converted into its 1-O-acetate 14. Hydrolysis of 12 in acetic acid-water afforded, after acetylation, 1,2,3-tri-O-acetyl-4-O-benzoyl-5-thio-L-ara-binopyranose 17 which was transformed into 2,3-di-O-acetyl-4-O-benzoyl-5-thio-L-arabinopyranosyl bromide 20. Zemplen deacylation of 17 gave 5-thio-L-arabinopyranose which was converted via 1,2,3,4-tetra-O-acetyl-5-thio-beta-L-arabinopyranose 5 into 2,3,4-tri-O-acetyl-5-thio-beta-L-arabinopyranosyl bromide 6 and into O-(2,3,4-tri-O-acetyl-5-thio-L-arabinopyranosyl) trichloro-acetimidate 7. Glycosidation of 4-nitrophenol with 12 under the Mitsunobu conditions afforded 4-nitrophenyl 4-O-benzoyl-2,3-O-isopropylidene-5-thio-alpha- and beta-L-arabinopyranoside in a similar to 1:2 ratio. Condensation of the glycosyl donors 6, 7, 17, and 20 with 4-cyano- and 4-nitrobenzenethiol yielded, after deacylation, 4-cyano- and 4-nitrophenyl 1,5-dithio-alpha- and beta-L-arabinopyranosides 28 alpha, 28 beta, 29 alpha and 29 beta in different ratios and yields, depending on the reaction conditions applied. In a similar manner the corresponding D-isomers 30 alpha, 30 beta, 31 alpha and 31 beta were also prepared. All of these glycosides, except 28 alpha, showed a stronger oral antithrombotic effect in rats as compared to beciparcil, used as reference. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00221-3
• 作为产物：
  描述：

  Acetic acid (3R,4S,5R)-4,5-diacetoxy-2-benzylsulfanyl-tetrahydro-thiopyran-3-yl ester 在 溴 作用下， 以 四氯化碳 为溶剂， 以76%的产率得到Acetic acid (2R,3R,4S,5R)-3,5-diacetoxy-2-bromo-tetrahydro-thiopyran-4-yl ester
  参考文献：
  名称：

  Synthesis of 5-thialdopentopyranoside via dithioacetal rearrangement and glycosidation to give pseudodisaccharides

  摘要：

  Rearrangement of acetylated 5-O-p-toluenesulfonyl-L-arabinose dibenzyl dithioacetal 10 gave benzyl 1,5-dithio-L-arabinopyranoside 6 which upon anomeric bromination followed by glycosidation led to pseudodisaccharide 20 containing a sulfur atom in the ring of the non-reducing unit Similarly, benzyl 1,5-dithio-D-lyxopyranoside 17 was obtained from 5-O-p-tolueresulfonyl-D-lyxose dibenzyl dithioacetal 16.

  DOI：

  10.1016/s0040-4039(00)73176-5