ethyl 2-(4',6'-di-O-benzyl-2',3'-dideoxy-α-D-erythro-hex-2'-enopyranosyl)-2(R,S)-nitroacetate | 113019-37-7

• 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: ethyl 2-(4',6'-di-O-benzyl-2',3'-dideoxy-α-D-erythro-hex-2'-enopyranosyl)-2(R,S)-nitroacetate
• 英文别名: ethyl 2-(2,3-dideoxy-4,6-di-O-benzyl-α-D-erythro-hex-2-enopyranosyl)-2(R,S)-nitroacetate；ethyl 2-(4,6-di-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-(2R,S)-nitroacetate；ethyl 2-(4,6-di-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-2(R,S)-nitroacetate；ethyl 2-nitro-2-[(2R,3S,6S)-3-phenylmethoxy-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran-6-yl]acetate
• CAS: 113019-37-7
• 化学式: C₂₄H₂₇NO₇
• 分子量: 441.481
• InChiKey: ZBOPJGXOZVRRNA-JYEDNEFCSA-N

物化性质

• 沸点：
  572.6±50.0 °C(predicted)
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  99.8
• 氢给体数：
  0
• 氢受体数：
  7

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)-nitroacetate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以30%的产率得到ethyl 2(R,S)-amino-2-(4,6-di-O-benzyl-2,3-dideoxy-α-D-erythro-hexopyranosyl)-2(R,S)-nitroacetate
  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：

  Acetic acid (2R,3S,6R)-2-acetoxymethyl-6-phenoxy-3,6-dihydro-2H-pyran-3-yl ester 在 氢氧化钾 、 sodium methylate 、 1,2-双(二苯基膦)乙烷 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 为溶剂， 反应 19.75h， 生成 ethyl 2-(4',6'-di-O-benzyl-2',3'-dideoxy-α-D-erythro-hex-2'-enopyranosyl)-2(R,S)-nitroacetate
  参考文献：
  名称：

  Palladium(0)-based approach to functionalized C-glycopyranosides

  摘要：

  DOI：

  10.1021/jo00269a026

文献信息

• Synthesis of the anomeric ethyl 2-(4,6-di-O-benzyl-2,3-dideoxy-d-erythro-hex-2-enopyranosyl)acetates and their structural characterization
  作者：Mohamed Brakta、Paul Lhoste、Denis Sinou、Joseph Banoub

  DOI：10.1016/0008-6215(90)80054-7

  日期：1990.8
• BRAKTA, MOHAMED;LHOSTE, PAUL;SINOU, DENIS, J. ORG. CHEM., 54,(1989) N, C. 1890-1896
  作者：BRAKTA, MOHAMED、LHOSTE, PAUL、SINOU, DENIS

  DOI：——

  日期：——
• BRAKTA, MOHAMED;LHOSTE, PAUL;SINOU, DENIS;BANOUB, JOSEPH, CARBOHYDR. RES., 203,(1990) N, C. 148-155
  作者：BRAKTA, MOHAMED、LHOSTE, PAUL、SINOU, DENIS、BANOUB, JOSEPH

  DOI：——

  日期：——
• SYNTHESIS OF UNSATURATED<i>C</i>-GLYCOSYL GLYCINES
  作者：Angelika Wernicke、Denis Sinou

  DOI：10.1081/car-100103957

  日期：2001.3.31

  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.
• Palladium(0)-based approach to functionalized C-glycopyranosides
  作者：Mohamed Brakta、Paul Lhoste、Denis Sinou

  DOI：10.1021/jo00269a026

  日期：1989.4