methyl 2,3,4-tri-O-acetyl-1-thio-α-L-arabinopyranoside | 84635-53-0

• 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: methyl 2,3,4-tri-O-acetyl-1-thio-α-L-arabinopyranoside
• 英文别名: methyl 2,3,4-tri-O-acetyl-1-thio-β-L-arabinopyranoside；p-tolyl 2,3,4-tri-O-acetyl-1-thio-β-L-arabinopyranoside；methyl-(tri-O-acetyl-1-thio-α-L-arabinopyranoside)；Methyl-(tri-O-acetyl-1-thio-α-L-arabinopyranosid)；[(3S,4S,5R,6S)-4,5-diacetyloxy-6-methylsulfanyloxan-3-yl] acetate
• CAS: 84635-53-0
• 化学式: C₁₂H₁₈O₇S
• 分子量: 306.337
• InChiKey: GGLGWBPMHHHYEX-YFKTTZPYSA-N

物化性质

• 熔点：
  73-74 °C
• 沸点：
  369.1±42.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-1-thio-α-L-arabinopyranoside 在 甲醇 、 sodium methylate 作用下， 生成 methyl-(1-thio-α-L-arabinopyranoside)
  参考文献：
  名称：

  Helferich et al., Chemische Berichte, 1953, vol. 86, p. 873

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-L-arabinopyranose 在 碘 、 六甲基二硅氮烷 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 methyl 2,3,4-tri-O-acetyl-1-thio-α-L-arabinopyranoside
  参考文献：
  名称：

  Streamlined Synthesis of Per-O-acetylated Sugars, Glycosyl Iodides, or Thioglycosides from Unprotected Reducing Sugars¹

  摘要：

  Solvent-free per-O-acetylation of sugars with stoichiometric acetic anhydride and catalytic iodine proceeds in high yield (90-99%) to give exclusively pyranose products as anomeric mixtures. Without workup, subsequent anomeric substitution employing iodine in the presence of hexamethyldisilane (i.e., TMS-I generated in situ) gives the corresponding glycosyl iodides in 75-95% isolated yield. Alternatively, and without workup, further treatment with dimethyl disulfide or thiol (ethanethiol or thiocresol) gives anomerically pure thioglycosides in more than 75% overall yield.

  DOI：

  10.1021/jo048890e

文献信息

• A Through-process for the Preparation of Methyl Per-<i>O</i>-acetyl 1-Thio-glycosides from Aldoses
  作者：Shinkiti Koto、Toyosaku Yoshida、Kazuhiro Takenaka、Shonosuke Zen

  DOI：10.1246/bcsj.55.3667

  日期：1982.11

  d-Glucose, d-galactose, d-mannose, d-xylose, l-arabinose, l-fucose, l-rhamnose, maltose, cellobiose, lactose, d-glucosamine, d-galactosamine, and d-mannosamine were converted into the corresponding methyl per-O-acetyl 1-thioglycopyranosides by way of a three-step (acetobromination, methylthioation, and acetylation) through-process in a single vessel.

  d-葡萄糖、d-半乳糖、d-甘露糖、d-木糖、l-阿拉伯糖、l-岩藻糖、l-鼠李糖、麦芽糖、纤维二糖、乳糖、d-葡萄糖胺、d-半乳糖胺和d-甘露糖胺通过一个反应器经过三步（溴乙酰化、甲硫化和乙酰化）转化为相应的甲基全乙酰化1-硫代糖呋喃糖苷。
• Reaction of sugar thiocyanates with Grignard reagents. New synthesis of thioglycosides.
  作者：Zbigniew Pakulski、Donat Pierożyński、Aleksander Zamojski

  DOI：10.1016/s0040-4020(01)87009-5

  日期：1994.2

  Glycosyl thiocyanates having hydroxyl groups protected with acetyl or benzoyl groups react readily at −40°C with Grignard reagents to afford the corresponding alkyl or aryl thioglycosides in good yields. Monosaccharide derivatives having the SCN grouping at other positions form under similar conditions thioethers. Axial thiocyanates do not react. Elevated temperatures induce side reactions leading

  在-40℃下，具有被乙酰基或苯甲酰基保护的羟基的糖基硫氰酸氰酸酯易于与格氏试剂反应，以高收率得到相应的烷基或芳基硫代糖苷。在相似条件下形成在其他位置具有SCN基团的单糖衍生物可形成硫醚。轴向硫氰酸盐不反应。升高的温度引起副反应，导致硫醇。
• A Facile and Efficient Method for the One-Pot Synthesis of Per-<i>O</i>-acetylated Thioglycosides from Unprotected Sugars
  作者：Shiqiang Yan、Ning Ding、Wei Zhang、Peng Wang、Yingxia Li、Ming Li

  DOI：10.1080/07328303.2012.673669

  日期：2012.9

  An efficient, convenient protocol for the preparation of per-O-acetylated p-tolylthio glycosides is described. Treatment of various unprotected sugars, including 2-deoxy-2-amino sugars, sialic acid, lactose, and maltose, with acetic anhydride using SnCl4 as a catalyst, and subsequently with p-tolylthiol, furnished the corresponding thioglycosides in 71%-90% yield under solvent-free conditions.