2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl dimethylphosphinothioate | 96863-21-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl dimethylphosphinothioate
• 英文别名: dimethyl-sulfanylidene-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-lambda5-phosphane；dimethyl-sulfanylidene-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-λ5-phosphane
• CAS: 96863-21-7
• 化学式: C₃₆H₄₁O₆PS
• 分子量: 632.758
• InChiKey: QCVCQKOZLHOWBK-SQGINLDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  44
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  87.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl dimethylphosphinothioate 生成 (2R,3R,4S,5R,6R)-2-[[(3S,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
  参考文献：
  名称：

  INADZU, TOSIYUKI

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,4,6-四苄基-D-吡喃葡萄糖 、 二甲基硫代磷酰氯 在 正丁基锂 作用下， 生成 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl dimethylphosphinothioate
  参考文献：
  名称：

  GLUCOSYLATION USING GLUCOPYRANOSYL DIMETHYLPHOSPHINOTHIOATE

  摘要：

  在过氯酸银存在的情况下，从2,3,4,6-四-O-苄基-α-D-吡喃葡萄糖基二甲基硫代膦酸酯和醇类中制备了几种葡萄糖苷，且收率良好。通过这种方法，主要获得了α-葡萄糖苷。

  DOI：

  10.1246/cl.1985.297

文献信息

• New Synthetic Methods and Reagents for Complex Carbohydrates. VII. Syntheses and Glycosylation Reactions of Glycopyranosyl Dimethylphosphinothioate Series Having a Nonparticipating Group at the C-2 Position
  作者：Takashi Yamanoi、Kazumi Nakamura、Shuji Sada、Masahiro Goto、Yoji Furusawa、Masaaki Takano、Ayumi Fujioka、Kenji Yanagihara、Yuzuru Satoh、Hideaki Hosokawa、Toshiyuki Inazu

  DOI：10.1246/bcsj.66.2617

  日期：1993.9

  nonparticipating group at the C-2 position could be easily prepared by reactions of the corresponding glycopyranose and dimethylphosphinothioyl chloride using butyllithium as a base in tetrahydrofuran. These dimethylphosphinothioates are stable at room temperature and gave the corresponding α-glycosides, predominantly in good yields, by reactions with alcohols using silver perchlorate as an activator in the

  在四氢呋喃中使用丁基锂作为碱，通过相应的吡喃糖和二甲基硫代膦酰氯反应，可以很容易地制备在 C-2 位具有非参与基团的几种吡喃糖基二甲基硫代膦酸酯。这些二甲基硫代膦酸酯在室温下是稳定的，并且在室温下在苯中的分子序列 4A 存在下，通过使用高氯酸银作为活化剂与醇反应，得到相应的 α-糖苷，主要是产率良好。此外，联合使用碘和催化量的高氯酸三苯甲酯作为一种新的活化系统而不是高氯酸银，对于这种糖苷化是有效的。此外，使用本方法制备了H-二糖和Lewis X抗原的合成中间体。
• New Synthetic Methods and Reagents for Complex Carbohydrates. IX. Aryl D-Glucopyranosides and 1-Aryl-1-deoxy-D-glucopyranoses from 2,3,4,6-Tetra-<i>O</i>-benzyl-<i>α</i>-D-glucopyranosyl Dimethylphosphinothioate
  作者：Takashi Yamanoi、Ayumi Fujioka、Toshiyuki Inazu

  DOI：10.1246/bcsj.67.1488

  日期：1994.5

  The reactions of 2,3,4,6-tetra-O-benzyl-α-d-glucopyranosyl dimethylphosphinothioate and phenolic compounds gave the corresponding aryl α-d-glucopyranosides predominantly in good yields, even when the trimethylsiloxy derivatives of benzene, which are known to afford 1-aryl-1-deoxy-d-glucopyranoses by the conventional methods, were used as acceptors. On the other hands, 1-ary-1-deoxy-β-d-glucopyranose was obtained in good yield when 1,3,5-trimethoxybenzene was used as an acceptor.

  2,3,4,6-四-O-苄基-α-d-吡喃葡萄糖基二甲基硫代磷酸酯与酚类化合物反应，主要得到相应的芳基α-d-吡喃葡萄糖苷，收率很高，即使使用苯的三甲基硅氧烷衍生物作为受体也是如此，众所周知，苯的三甲基硅氧烷衍生物可通过传统方法得到 1-芳基-1-脱氧-d-吡喃葡萄糖。另一方面，以 1,3,5-三甲氧基苯为受体时，1-芳基-1-脱氧-β-d-吡喃葡萄糖的产率也很高。
• GLUCOSYLATION USING GLUCOPYRANOSYL DIMETHYLPHOSPHINOTHIOATE
  作者：Toshiyuki Inazu、Hideaki Hosokawa、Yuzuru Satoh

  DOI：10.1246/cl.1985.297

  日期：1985.3.5

  Several glucosides were prepared in good yields from 2,3,4,6-tetra-o -benzyl-α-d-glucopyranosyl dimethylphosphinothioate and alcohols in the presence of silver perchlorate. By this method α-glucosides were predominantly obtained.

  在过氯酸银存在的情况下，从2,3,4,6-四-O-苄基-α-D-吡喃葡萄糖基二甲基硫代膦酸酯和醇类中制备了几种葡萄糖苷，且收率良好。通过这种方法，主要获得了α-葡萄糖苷。
• INADZU, TOSIYUKI
  作者：INADZU, TOSIYUKI

  DOI：——

  日期：——