tert-butyldimethylsilyl 4-O-acetyl-2,3-di-O-benzoyl-6-S-phenyl-6-thio-α-D-glucopyranoside | 291774-88-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyldimethylsilyl 4-O-acetyl-2,3-di-O-benzoyl-6-S-phenyl-6-thio-α-D-glucopyranoside
• 英文别名: tert-butyldimethylsilyl 4-O-acetyl-2,3-di-O-benzoyl-6-phenylthio-6-deoxy-α-D-glucopyranoside；Bz(-2)[Bz(-3)][PhS(-6d)]Glc4Ac(a)-O-TBDMS；[(2R,3R,4S,5S,6S)-5-acetyloxy-3-benzoyloxy-2-[tert-butyl(dimethyl)silyl]oxy-6-(phenylsulfanylmethyl)oxan-4-yl] benzoate
• CAS: 291774-88-4
• 化学式: C₃₄H₄₀O₈SSi
• 分子量: 636.838
• InChiKey: DAEJXYIYCYLNGV-PMBNRAAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.91
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyldimethylsilyl 4-O-acetyl-2,3-di-O-benzoyl-6-S-phenyl-6-thio-α-D-glucopyranoside 在 吡啶 、 磺酰氯 、 4 Angstroem MS 、 四丁基氟化铵 、 溶剂黄146 、 mercury dichloride 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 12.0h， 生成 methyl (diosgenin-3β-yl 4-O-acetyl-2,3-di-O-benzoyl-β-D-glucopyranoside)uronate
  参考文献：
  名称：

  A Novel and Effective Procedure for the Preparation of Glucuronides

  摘要：

  [GRAPHICS]6-Phenylthio-6-deoxy D-glucopyranosides were easily prepared from 6-hydroxy-D-glucopyranosides and employed as effective glycosyl donors or accepters. And the resulting coupling products were then readily converted into the corresponding D-glucuronide-containing compounds.

  DOI：

  10.1021/ol0062143
• 作为产物：
  描述：

  在 三丁基膦 作用下， 以 吡啶 为溶剂， 反应 24.0h， 生成 tert-butyldimethylsilyl 4-O-acetyl-2,3-di-O-benzoyl-6-S-phenyl-6-thio-α-D-glucopyranoside
  参考文献：
  名称：

  A Novel and Effective Procedure for the Preparation of Glucuronides

  摘要：

  [GRAPHICS]6-Phenylthio-6-deoxy D-glucopyranosides were easily prepared from 6-hydroxy-D-glucopyranosides and employed as effective glycosyl donors or accepters. And the resulting coupling products were then readily converted into the corresponding D-glucuronide-containing compounds.

  DOI：

  10.1021/ol0062143

文献信息

• 6-S-Phenyl-glycopyranosides as ready precursors to the synthesis of glycuronides
  作者：Biao Yu、Xiangming Zhu、Yongzheng Hui

  DOI：10.1016/s0040-4020(01)00959-0

  日期：2001.11

  6-S-Phenyl-gluco/galactopyranosides, readily prepared from the corresponding 6-hydroxy-glycosides, were demonstrated to be effective glycosyl donors or acceptors. The resulting coupling products were then easily converted into the corresponding glycuronidecontaining compounds under mild conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.