methyl 2-O-acetyl-3,4-O-carbonyl-β-L-arabinopyranoside | 111476-58-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: methyl 2-O-acetyl-3,4-O-carbonyl-β-L-arabinopyranoside
• 英文别名: [(3aS,6S,7R,7aS)-6-methoxy-2-oxo-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl] acetate
• CAS: 111476-58-5
• 化学式: C₉H₁₂O₇
• 分子量: 232.19
• InChiKey: KPZATBWRYFWTJD-HSNKUXOKSA-N

物化性质

• 沸点：
  397.4±42.0 °C(predicted)
• 密度：
  1.38±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  Methyl-2-O-acetyl-3,4-O-thiocarbonyl-β-L-arabinopyranosid 在 二正丁基氧化锡 作用下， 以 1,4-二氧六环 为溶剂， 以80%的产率得到methyl 2-O-acetyl-3,4-O-carbonyl-β-L-arabinopyranoside
  参考文献：
  名称：

  Utilization of Sugars in Organic Synthesis. Part XXV. Conversion of Thiocarbonyl into Carbonyl Group by O-S Exchange Reaction with Dibutyltin Oxide or Bistributyltin Oxide.

  摘要：

  加热环状硫代碳酸酯和硫代内酯与1.0-1.5摩尔当量的二丁基氧化锡或二特丁基氧化锡在二恶烷中，分别以良好的产率得到相应的碳酸酯和内酯。

  DOI：

  10.1248/cpb.40.1033

文献信息

• Utilization of Sugars in Organic Synthesis. Part XXXIII. Thio-Sugars III. Radical Catalyzed Thione-Thiol Rearrangement of Cyclic Thionocarbonates on a Pyranose Ring: Formation of cis-Arranged Cyclic Thiolcarbonates.
  作者：Yoshisuke TSUDA、Shinsuke NOGUCHI、Kimihiro KANEMITSU、Yoshiyuki SATO、Kyoko KAKIMOTO、Yumiko IWAKURA、Shinzo HOSOI

  DOI：10.1248/cpb.45.971

  日期：——

  Pyranoside 3, 4-cis-thionocarbonates, under radical-promoted reaction conditions (method A, B, or C, described in the text), gave O-S rearrangement products, 3, 4-thiolcarbonates of cis-stereochemistry, in accepTable yields.2, 3-Thionocarbonates of trans-stereochemistry also gave the rearrangement products of cis-stereochemistry preferentially in method B (photolysis with hexabutyldistannane). Although regio-control of the product was not satisfactory in most cases, some of the results suggested that the regioselectivity of the reaction is markedly influenced by the stereochemistry of the anomeric position of the substrates. The products were converted to thioglycosides(peracetate forms) by conventional means.

  吡喃糖苷 3, 4-顺式硫代碳酸酯在自由基促进的反应条件下（方法 A、B 或 C，如本文所述）以可接受的产率生成 O-S 重排产物，即顺式立体化学的 3, 4-硫醇碳酸酯。2在方法B（用六丁基二锡烷光解）中，反式立体化学的3-硫代碳酸酯也优先产生顺式立体化学的重排产物。尽管在大多数情况下产物的区域控制并不令人满意，但一些结果表明反应的区域选择性明显受到底物异头位置的立体化学的影响。通过常规方法将产物转化为硫代糖苷（全乙酸盐形式）。
• Haque, Ekramul Mohammed; Kikuchi, Tohru; Kanemitsu, Kimihiro, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 3, p. 1016 - 1029
  作者：Haque, Ekramul Mohammed、Kikuchi, Tohru、Kanemitsu, Kimihiro、Tsuda, Yoshisuke

  DOI：——

  日期：——
• Kanemitsu, Kimihiro; Tsuda, Yoshisuke; Haque, Mohammed Ekramul, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 9, p. 3874 - 3879
  作者：Kanemitsu, Kimihiro、Tsuda, Yoshisuke、Haque, Mohammed Ekramul、Tsubono, Koji、Kikuchi, Tohru

  DOI：——

  日期：——
• Tsuda, Yoshisuke; Kanemitsu, Kimihiro; Kakimoto, Kyoko, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 5, p. 2148 - 2150
  作者：Tsuda, Yoshisuke、Kanemitsu, Kimihiro、Kakimoto, Kyoko、Kikuchi, Tohru

  DOI：——

  日期：——
• KANEMITSU, KIMIHIRO;TSUDA, YOSHISUKE;HAQUE, MOHAMMED EKRAMUL;TSUBONO, KOJ+, CHEM. AND PHARM. BULL., 35,(1987) N 9, 3874-3879
  作者：KANEMITSU, KIMIHIRO、TSUDA, YOSHISUKE、HAQUE, MOHAMMED EKRAMUL、TSUBONO, KOJ+

  DOI：——

  日期：——