tert-butyl N-[(2R,3R,4S)-3,4-bis(methoxymethoxy)-5-oxo-1-trityloxypentan-2-yl]carbamate | 1053452-26-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: tert-butyl N-[(2R,3R,4S)-3,4-bis(methoxymethoxy)-5-oxo-1-trityloxypentan-2-yl]carbamate
• CAS: 1053452-26-8
• 化学式: C₃₃H₄₁NO₈
• 分子量: 579.69
• InChiKey: JRMDZWBZLBDVIR-IDZRBWSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  42
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2R,3R,4S)-3,4-bis(methoxymethoxy)-5-oxo-1-trityloxypentan-2-yl]carbamate 在 sodium tetrahydroborate 、 copper bromide*dimethyl sulfide 、 potassium tert-butylate 、 臭氧 、 三乙胺 、 N,N-二乙基苯胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 50.33h， 生成 (2R,3R,4R,5S)-3,4,5-Tris-methoxymethoxy-2-trityloxymethyl-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Improved Synthesis of 1-Deoxynojirimycin and Facile Synthesis of Its Stereoisomers from (S)-Pyroglutamic Acid Derivative

  摘要：

  Improved synthesis of 1-deoxynojirimycin (9) from (E)-alpha,beta-unsaturated ester(1) and facile synthesis of 1-deoxyazasugars (14 and 15) from 10 where both substrates (1 and 10) prepared from (S)-pyroglutamic acid were described.

  DOI：

  10.3987/com-97-s11
• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 草酰氯 、 二甲基亚砜 、 三乙胺 、 N,N-二乙基苯胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 43.67h， 生成 tert-butyl N-[(2R,3R,4S)-3,4-bis(methoxymethoxy)-5-oxo-1-trityloxypentan-2-yl]carbamate
  参考文献：
  名称：

  Synthesis of (2R, 3R, 4R, 5R)-3,4-Dihydroxy-2,5-dihydroxymethylpyrrolidine and (-)-Anisomycin Derivative from (S)-Pyroglutamic Acid Derivative

  摘要：

  Double asymmetric dihydroxylation of (E)-alpha,beta-unsaturated ester(2) with a catalytic amount of potassium osmate and chiral ligand gave dihydroxy compounds (3a and 4a) selectively. Polyhydroxylated pyrrolidines (10 and 14) were synthesized from corresponding methoxymethy ether (3c) and tert-butyl-dimethylsilyl ether(4d), respectively.

  DOI：

  10.3987/com-94-7016

文献信息

• Improved Synthesis of 1-Deoxynojirimycin and Facile Synthesis of Its Stereoisomers from (S)-Pyroglutamic Acid Derivative
  作者：Nobuo Ikota、Jun-ichi Hirano、Ranjith Gamage、Hidehiko Nakagawa、Hiroko Hama-Inaba

  DOI：10.3987/com-97-s11

  日期：——

  Improved synthesis of 1-deoxynojirimycin (9) from (E)-alpha,beta-unsaturated ester(1) and facile synthesis of 1-deoxyazasugars (14 and 15) from 10 where both substrates (1 and 10) prepared from (S)-pyroglutamic acid were described.
• Synthesis of (2R, 3R, 4R, 5R)-3,4-Dihydroxy-2,5-dihydroxymethylpyrrolidine and (-)-Anisomycin Derivative from (S)-Pyroglutamic Acid Derivative
  作者：Nobuo Ikota

  DOI：10.3987/com-94-7016

  日期：——

  Double asymmetric dihydroxylation of (E)-alpha,beta-unsaturated ester(2) with a catalytic amount of potassium osmate and chiral ligand gave dihydroxy compounds (3a and 4a) selectively. Polyhydroxylated pyrrolidines (10 and 14) were synthesized from corresponding methoxymethy ether (3c) and tert-butyl-dimethylsilyl ether(4d), respectively.