[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(tributyl-lambda5-phosphanylidene)amino]oxan-2-yl]methyl acetate | 353264-29-6

• 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: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(tributyl-lambda5-phosphanylidene)amino]oxan-2-yl]methyl acetate
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(tributyl-λ5-phosphanylidene)amino]oxan-2-yl]methyl acetate
• CAS: 353264-29-6
• 化学式: C₂₆H₄₆NO₉P
• 分子量: 547.626
• InChiKey: XAEGZQJXEOKFIE-WSGIOKLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  37
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(tributyl-lambda5-phosphanylidene)amino]oxan-2-yl]methyl acetate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2,3,4,6-Tetra-O-acetyl-N-(S-acetylmercaptoacetyl)-β-D-glucopyranosylamine
  参考文献：
  名称：

  Synthesis of ClusterN-Glycosides Based on aβ-Cyclodextrin Core

  摘要：

  A convenient method for the synthesis of beta-D-gluco-, beta-D-galacto-, 2-acetamido-2-deoxy-beta-D-gluco- and alpha-D-mannopyranosylamine clusters based on cyclomaltoheptaose (beta-cyclodextrin) is presented. The synthesis involves: 1) the one-pot synthesis of the acetylated chloroacetyl N-glycoside derivatives of D-glucose, D-galactose, 2-acetamido-2-deoxy-D-glucose and D-mannose from the corresponding glycosyl azides, 2) conversion of the chloroacetyl N-glycosides into their isothiouronium derivatives, then 3) attachment of the N-glycosides onto heptakis(6-deoxy-6-iodo) and heptakis(6-chloroacetamido-6-deoxy) beta-cyclodextrin by means of nucleophilic displacement with caesiurn carbonate in dimethylformamide, and 4) de-O-acetylation of beta-cyclodextrin derivatives. The chloroacetyl N-glycoside derivatives were easily prepared by mild reduction of the azide function by one of two methods: a) by the Staudinger reaction, with nBu(3)P, and b) with 1,3-propanedithiol, as reducing reagents.

  DOI：

  10.1002/(sici)1521-3765(19990604)5:6<1775::aid-chem1775>3.0.co;2-2
• 作为产物：
  描述：

  三丁基膦 、 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(tributyl-lambda5-phosphanylidene)amino]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  Synthesis of ClusterN-Glycosides Based on aβ-Cyclodextrin Core

  摘要：

  A convenient method for the synthesis of beta-D-gluco-, beta-D-galacto-, 2-acetamido-2-deoxy-beta-D-gluco- and alpha-D-mannopyranosylamine clusters based on cyclomaltoheptaose (beta-cyclodextrin) is presented. The synthesis involves: 1) the one-pot synthesis of the acetylated chloroacetyl N-glycoside derivatives of D-glucose, D-galactose, 2-acetamido-2-deoxy-D-glucose and D-mannose from the corresponding glycosyl azides, 2) conversion of the chloroacetyl N-glycosides into their isothiouronium derivatives, then 3) attachment of the N-glycosides onto heptakis(6-deoxy-6-iodo) and heptakis(6-chloroacetamido-6-deoxy) beta-cyclodextrin by means of nucleophilic displacement with caesiurn carbonate in dimethylformamide, and 4) de-O-acetylation of beta-cyclodextrin derivatives. The chloroacetyl N-glycoside derivatives were easily prepared by mild reduction of the azide function by one of two methods: a) by the Staudinger reaction, with nBu(3)P, and b) with 1,3-propanedithiol, as reducing reagents.

  DOI：

  10.1002/(sici)1521-3765(19990604)5:6<1775::aid-chem1775>3.0.co;2-2