ethyl 2-(4,6-di-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-2(R,S)-[(N-diphenylmethylene)amino]acetate | 361448-61-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-(4,6-di-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-2(R,S)-[(N-diphenylmethylene)amino]acetate
• 英文别名: ethyl 2-(benzhydrylideneamino)-2-[(2R,3S,6S)-3-phenylmethoxy-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran-6-yl]acetate
• CAS: 361448-61-5
• 化学式: C₃₇H₃₇NO₅
• 分子量: 575.704
• InChiKey: MRHJTVSHMBZFIR-GLKLMELYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.58
• 重原子数：
  43.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  66.35
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4,6-di-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-2(R,S)-[(N-diphenylmethylene)amino]acetate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 ethyl 2-(4,6-di-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-2-(benzhydrylamino)acetate
  参考文献：
  名称：

  SYNTHESIS OF UNSATURATEDC-GLYCOSYL GLYCINES

  摘要：

  Palladium(0)-catalyzed alkylation of 2,3-unsaturated aryl glycoside with ethyl nitroacetace or N-(dipheuylmethylene)glycine ethyl ester in the presence of N,O-bis(trimethylsilyl)acetamide/KOAc afforded ethyl 2-(4,5-di-O-benzyl-2,3-dideoxy-alpha -D-erythro-hex-2-enopyranosyl)-2(R,S)-nitroacetate (2) and ethyl 3-(4,6-di-O-benzyl-2,3-dideoxy-alpha -D-erythro-hex-2-enopyranosyl)-2(R,S)-[(N-diphenylmethylene)amino)]acetate (7), respectively. Hydrogenation of compound 2 afforded the saturated aminoesters, while compound 7 was readily transformed into 2-(4,6-di-O-benzyl-2,3-dideoxy-alpha -D-erythro-hex-2-enopyranosyl)-2(R,S)-glycine (10) by acidic hydrolysis followedby saponification.

  DOI：

  10.1081/car-100103957
• 作为产物：
  描述：

  二苯亚甲基甘氨酸乙酯 、 p-tert-butylphenyl 4,6-di-O-benzyl-2,3-dideoxy-α,β-D-erythro-hex-2-enopyranoside 在 tris(dibenzylideneacetone)dipalladium (0) 苯磺酰胺 、 potassium acetate 、 1,4-双(二苯基膦)丁烷 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到ethyl 2-(4,6-di-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-2(R,S)-[(N-diphenylmethylene)amino]acetate
  参考文献：
  名称：

  SYNTHESIS OF UNSATURATEDC-GLYCOSYL GLYCINES

  摘要：

  Palladium(0)-catalyzed alkylation of 2,3-unsaturated aryl glycoside with ethyl nitroacetace or N-(dipheuylmethylene)glycine ethyl ester in the presence of N,O-bis(trimethylsilyl)acetamide/KOAc afforded ethyl 2-(4,5-di-O-benzyl-2,3-dideoxy-alpha -D-erythro-hex-2-enopyranosyl)-2(R,S)-nitroacetate (2) and ethyl 3-(4,6-di-O-benzyl-2,3-dideoxy-alpha -D-erythro-hex-2-enopyranosyl)-2(R,S)-[(N-diphenylmethylene)amino)]acetate (7), respectively. Hydrogenation of compound 2 afforded the saturated aminoesters, while compound 7 was readily transformed into 2-(4,6-di-O-benzyl-2,3-dideoxy-alpha -D-erythro-hex-2-enopyranosyl)-2(R,S)-glycine (10) by acidic hydrolysis followedby saponification.

  DOI：

  10.1081/car-100103957