5-S-(benzothiazol-2-yl)-1,2-O-isopropylidene-5-thio-α-D-xylofuranose | 189274-93-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 5-S-(benzothiazol-2-yl)-1,2-O-isopropylidene-5-thio-α-D-xylofuranose
• 英文别名: (3aR,5S,6R,6aR)-5-(1,3-benzothiazol-2-ylsulfanylmethyl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS: 189274-93-9
• 化学式: C₁₅H₁₇NO₄S₂
• 分子量: 339.436
• InChiKey: BUNGFMFKKIZHLX-GWNIPJSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-S-(benzothiazol-2-yl)-1,2-O-isopropylidene-5-thio-α-D-xylofuranose 在 potassium tert-butylate 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 3-O-(benzothiazol-2-yl)-5-deoxy-1,2-O-isopropylidene-5-methylsulfonyl-α-D-xylofuranose
  参考文献：
  名称：

  A New Intramolecular Migration in Thiosugar Chemistry: S → O Transfer of a Benzothiazol-2-Yl Group in Saccharidic Sulfones

  摘要：

  Saccharidic benzothiazol-2yl sulfones - readily obtained through regioselective Mitsunobu thiofunctionalization followed by standard S-oxidation - can easily undergo benzothiazol-2-yl group S --> O transfer when submitted to the action of a hindered base under controlled conditions. An ipso-substitution process is the key-step of this novel intramolecular rearrangement of saccharidic sulfones.

  DOI：

  10.1080/07328309908543998
• 作为产物：
  描述：

  1,2-O-异亚丙基-alpha-D-呋喃木糖 、 2-巯基苯并噻唑 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 吡啶 为溶剂， 反应 0.33h， 以80%的产率得到5-S-(benzothiazol-2-yl)-1,2-O-isopropylidene-5-thio-α-D-xylofuranose
  参考文献：
  名称：

  Mechanism of Regioselective Mitsunobu Thiofunctionalization of Pentofuranoses

  摘要：

  Triphenylphosphine and diethyl azodicarboxylate react with 1,2-O-isopropylidene-alpha-D-xylo-(1) and ribofuranose (2) to give six-membered-ring phosphoranes. Xylofuranose 1 undergoes cyclodehydration to produce oxetane 17 in 85% yield, but ribofuranose 2 gives a pyrazolidine derivative 19 in 80% yield. Tn the presence of 2-mercaptobenzothiazole, the desired 5-S-(benzothiazol-2-yl)-5-thio derivatives 3 and 4 were isolated in 80% yield. P-31 NMR examination of this Mitsunobu thiofunctionalization reveals the presence of an alkoxytriphenylphosphonium species as the most stable intermediate which reacts with the thio-nucleophile via S(N)2 in a rate limiting step.

  DOI：

  10.1080/07328309708006514

文献信息

• Mechanism of Regioselective Mitsunobu Thiofunctionalization of Pentofuranoses
  作者：Jitka Moravcová、Patrick Rollin、Christelle Lorin、Vincent Gardon、Jindra Čapková、Jiří Mazáč

  DOI：10.1080/07328309708006514

  日期：1997.2

  Triphenylphosphine and diethyl azodicarboxylate react with 1,2-O-isopropylidene-alpha-D-xylo-(1) and ribofuranose (2) to give six-membered-ring phosphoranes. Xylofuranose 1 undergoes cyclodehydration to produce oxetane 17 in 85% yield, but ribofuranose 2 gives a pyrazolidine derivative 19 in 80% yield. Tn the presence of 2-mercaptobenzothiazole, the desired 5-S-(benzothiazol-2-yl)-5-thio derivatives 3 and 4 were isolated in 80% yield. P-31 NMR examination of this Mitsunobu thiofunctionalization reveals the presence of an alkoxytriphenylphosphonium species as the most stable intermediate which reacts with the thio-nucleophile via S(N)2 in a rate limiting step.
• A New Intramolecular Migration in Thiosugar Chemistry: S → O Transfer of a Benzothiazol-2-Yl Group in Saccharidic Sulfones
  作者：David Gueyrard、Christelle Lorin、Patrick Rollin、Jitka Moravcova

  DOI：10.1080/07328309908543998

  日期：1999.1.1

  Saccharidic benzothiazol-2yl sulfones - readily obtained through regioselective Mitsunobu thiofunctionalization followed by standard S-oxidation - can easily undergo benzothiazol-2-yl group S --> O transfer when submitted to the action of a hindered base under controlled conditions. An ipso-substitution process is the key-step of this novel intramolecular rearrangement of saccharidic sulfones.