2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl P,P-diphenyl-N-(p-toluenesulfonyl)phosphinimidate | 134637-13-1

• 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: 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl P,P-diphenyl-N-(p-toluenesulfonyl)phosphinimidate
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-tribenzoyloxy-6-[(4-methylphenyl)sulfonylimino-diphenyl-lambda5-phosphanyl]oxyoxan-2-yl]methyl benzoate；[(2R,3R,4S,5R,6S)-3,4,5-tribenzoyloxy-6-[(4-methylphenyl)sulfonylimino-diphenyl-λ5-phosphanyl]oxyoxan-2-yl]methyl benzoate
• CAS: 134637-13-1
• 化学式: C₅₃H₄₄NO₁₂PS
• 分子量: 949.972
• InChiKey: WHQRYUUSWCXVRL-MHUUICKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  68
• 可旋转键数：
  19
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  179
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl P,P-diphenyl-N-(p-toluenesulfonyl)phosphinimidate 、 鬼臼毒素 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以76%的产率得到podophyllotoxinyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  A new and general glycosidation method for podophyllum lignan glycosides

  摘要：

  A facile and stereocontrolled construction of beta-glycosidic linkages of podophyllotoxin and 4'-O-demethylepipodophyllotoxin D-glucosides or 4'-O-demethylepipodophyllotoxin 2-amino-2-deoxy-D-glucoside has been achieved by exploiting glycopyranosyl P,P-diphenyl-N-(p-toluene-sulfonyl)phosphinimidate and bis(dimethylamido) phosphate as glycosyl donors, respectively.

  DOI：

  10.1016/s0040-4039(00)74296-1
• 作为产物：
  描述：

  [(3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxythallium 、 N-(p-Toluolsulfonyl)-chlor-diphenyl-phosphinimin 生成 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl P,P-diphenyl-N-(p-toluenesulfonyl)phosphinimidate
  参考文献：
  名称：

  HASHIMOTO, SHUN-ICHI;HONDA, TAKESHI;IKEGAMI, SHIRO, HETEROCYCLES, 30,(1990) N, C. 775-778

  摘要：

  DOI：

文献信息

• Oligosaccharide synthesis based on glycosyl donors and acceptors carrying phosphorus-containing leaving groups
  作者：Shun-ichi Hashimoto、Hiroki Sakamoto、Takeshi Honda、Shiro Ikegami

  DOI：10.1016/s0040-4039(97)01122-2

  日期：1997.7

  Efficient synthetic strategy for oligosaccharides has been developed by exploiting the difference in anomeric reactivity between glycosyl donors and acceptors carrying phosphorus-containing leaving groups, wherein the tetramethylphosphoroamidate group plays a pivotal role as anomeric protective group as well as leaving group.

  通过利用糖基供体和带有含磷离去基团的受体之间的异头反应性的差异，开发了一种有效的寡糖合成策略，其中四甲基磷酸氨基甲酸酯基团作为异头保护基团和离去基团起着关键作用。
• A new and general glycosidation method for podophyllum lignan glycosides
  作者：Shun-ichi Hashimoto、Takeshi Honda、Shiro Ikegami

  DOI：10.1016/s0040-4039(00)74296-1

  日期：1991.3

  A facile and stereocontrolled construction of beta-glycosidic linkages of podophyllotoxin and 4'-O-demethylepipodophyllotoxin D-glucosides or 4'-O-demethylepipodophyllotoxin 2-amino-2-deoxy-D-glucoside has been achieved by exploiting glycopyranosyl P,P-diphenyl-N-(p-toluene-sulfonyl)phosphinimidate and bis(dimethylamido) phosphate as glycosyl donors, respectively.
• HASHIMOTO, SHUN-ICHI;HONDA, TAKESHI;IKEGAMI, SHIRO, HETEROCYCLES, 30,(1990) N, C. 775-778
  作者：HASHIMOTO, SHUN-ICHI、HONDA, TAKESHI、IKEGAMI, SHIRO

  DOI：——

  日期：——