1,2,3,4-tetra-O-acetyl-5-thio-β-L-arabinopyranose | 96863-07-9

• 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: 1,2,3,4-tetra-O-acetyl-5-thio-β-L-arabinopyranose
• 英文别名: [(3R,4S,5R,6S)-4,5,6-triacetyloxythian-3-yl] acetate
• CAS: 96863-07-9
• 化学式: C₁₃H₁₈O₈S
• 分子量: 334.347
• InChiKey: JEGLENJOJVLAIW-RVMXOQNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetra-O-acetyl-5-thio-β-L-arabinopyranose 在 4 A molecular sieve 、 三氟化硼乙醚 、 乙酸肼 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.75h， 生成 [(3R,4S,5R,6R)-4,5-diacetyloxy-6-(4-cyanophenyl)sulfanylthian-3-yl] acetate
  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：

  5-S-Benzoyl-2,3-O-isopropylidene-5-thio-L-arabinose 在 吡啶 、 水 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 1,2,3,4-tetra-O-acetyl-5-thio-β-L-arabinopyranose
  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

文献信息

• Synthesis of 5-thio-d-arabinose and 5-thio-d-lyxose and their methyl glycopyranosides
  作者：Neil A. Hughes、Namboole M. Munkombwe

  DOI：10.1016/0008-6215(85)85213-7

  日期：1985.2

  Abstract 1,2- O -Isopropylidene-5- O -toluene- p -sulphonyl-β- d -arabinofuranose has been converted into 5-thio- d -arabinose via 3- O -acetyl-5- S -acetyl-1,2- O -isopropylidene-5-thio-β- d -arabinofuranose. 5-Thio- d -lyxose was similarly obtained from methyl 2,3- O -isopropylidene-5- O -methanesulphonyl(or toluene- p -sulphonyl)-α- d -lyxofuranoside via methyl 5- S -acetyl(or benzoyl)-1,2- O -

  摘要1,2-O-异亚丙基-5-O-甲苯基-对-磺酰基-β-d-阿拉伯呋喃糖已通过3-O-乙酰基-5-S-乙酰基-1转化为5-硫代-d-阿拉伯糖， 2-O-异亚丙基-5-硫代-β-d-呋喃糖。类似地，由甲基2，3-O-异亚丙基-5-O-甲磺酰基（或甲苯-对-磺酰基）-α-d-呋喃呋喃糖苷经由5-S-乙酰基（或苯甲酰基）甲基获得5-噻吩基-二糖。 -1,2-O-异亚丙基-5-硫代-α-d-呋喃呋喃糖苷。通过游离糖或上述硫代酯中间体的甲醇分解获得相应的甲基硫代吡喃糖苷。现在已经知道所有的5-硫代-d-戊吡喃糖及其甲基的5-硫代-d-戊吡喃糖苷，并且总结了它们的一些特性。
• [EN] NOVEL ANTICOAGULANT GLYCOSIDES AND PHARMACEUTICAL COMPOSITIONS THEREOF<br/>[FR] NOUVEAUX GLYCOSIDES ANTICOAGULANTS ET LEURS COMPOSITIONS PHARMACEUTIQUES
  申请人：RICHTER GEDEON VEGYÉSZETI GYÁR RT.

  公开号：WO1999028312A1

  公开（公告）日：1999-06-10

  (EN) This invention relates to novel 1,5-dithio-L- and D-arabinopyranosides of formula (I), wherein R represents a cyano, nitro, aminothiocarbonyl, amidino or an acetamido group and the acid addition salts thereof formed with organic or inorganic acids, if possible as well as pharmaceutical compositions containing them. The compounds of the invention possess valuable therapeutic, particularly anticoagulant properties.(FR) L'invention concerne de nouveaux 1,5-dithio-L- et D-arabinopyrannosides de formule (I), dans laquelle R représente un cyano, nitro, aminothiocarbonyle, aminido ou un groupe acétamide et leurs sels d'addition d'acide formés, de préférence, avec des acides organiques ou inorganiques et des compositions pharmaceutiques les contenant. Les composés possèdent des propriétés thérapeutiques et plus spécifiquement anticoagulantes.

  该发明涉及公式(I)的新型1,5-二硫基-L-和D-阿拉比诺吡喃糖苷，其中R代表氰基、硝基、氨基硫酰基、酰胺基或乙酰胺基，以及它们与有机或无机酸形成的酸加成盐，如有可能，以及包含它们的药物组合物。该发明的化合物具有有价值的治疗特性，特别是抗凝血性质。