ethyl 2-(4-O-benzyl-2,3,6-trideoxy-α-L-erythro-hex-2-enopyranosyl)-2(R,S)-nitroacetate | 361448-59-1

• 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-O-benzyl-2,3,6-trideoxy-α-L-erythro-hex-2-enopyranosyl)-2(R,S)-nitroacetate
• 英文别名: ethyl 2-[(2S,3R,6R)-2-methyl-3-phenylmethoxy-3,6-dihydro-2H-pyran-6-yl]-2-nitroacetate
• CAS: 361448-59-1
• 化学式: C₁₇H₂₁NO₆
• 分子量: 335.357
• InChiKey: VAYADLYHEBNMMS-FZRMUPSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-O-benzyl-2,3,6-trideoxy-α-L-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-(4-O-benzyl-2,3,6-trideoxy-α-L-erythro-hexopyranosyl)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：

  硝基乙酸乙酯 、 p-tert-butylphenyl 4-O-benzyl-6-deoxy-2,3-dideoxy-α-L-erythro-hex-2-enopyranoside 在 tris(dibenzylideneacetone)dipalladium (0) 1,4-双(二苯基膦)丁烷 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到ethyl 2-(4-O-benzyl-2,3,6-trideoxy-α-L-erythro-hex-2-enopyranosyl)-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

文献信息

• THE SYNTHESIS OF C-9 MODIFIED DERIVATIVES OF THE α-METHYL GLYCOSIDE OF KDN METHYL ESTER
  作者：Adele K. Norton、Gaik B. Kok、Mark von Itzstein

  DOI：10.1081/car-100103960

  日期：2001.3.31

  The synthesis of a range of C-9 substituted derivatives of the cc-methyl glycoside of KDN methyl ester (2) is reported. 9-Deoxy-9-iodo, 9-deoxy-9 thioacetyl and 9-azido-9-deoxy derivatives (compounds 10, 12 and 13) were all prepared from the corresponding 9-O-tosylate 8. Catalytic hydrogenation of 10 and 13 results in reduction to give the 9-deoxy and 9-amino-9-deoxy derivatives 20 and 15, respectively. Further derivatisation of the amine 15 into compounds 17 and 18 was achieved via standard acylation procedures.