((1R,2R,3R,4R)-4-Hydroxy-2,3-bis-methoxymethoxy-1-trityloxymethyl-hex-5-enyl)-carbamic acid tert-butyl ester | 165879-59-4

• 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: ((1R,2R,3R,4R)-4-Hydroxy-2,3-bis-methoxymethoxy-1-trityloxymethyl-hex-5-enyl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2R,3R,4R,5R)-5-hydroxy-3,4-bis(methoxymethoxy)-1-trityloxyhept-6-en-2-yl]carbamate
• CAS: 165879-59-4
• 化学式: C₃₅H₄₅NO₈
• 分子量: 607.744
• InChiKey: UKURTNFRBRVSOR-SEVDZJIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  44
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ((1R,2R,3R,4R)-4-Hydroxy-2,3-bis-methoxymethoxy-1-trityloxymethyl-hex-5-enyl)-carbamic acid tert-butyl ester 在 sodium tetrahydroborate 、 TEA 、 臭氧 、 甲基磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 生成 (2S,3R,4R,5R)-2-Hydroxymethyl-3,4-bis-methoxymethoxy-5-trityloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester
  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
• 作为产物：
  描述：

  tert-butyl N-[(2R,3R,4R)-5-hydroxy-3,4-bis(methoxymethoxy)-1-trityloxypentan-2-yl]carbamate 在 copper bromide*dimethyl sulfide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 生成 ((1R,2R,3R,4R)-4-Hydroxy-2,3-bis-methoxymethoxy-1-trityloxymethyl-hex-5-enyl)-carbamic 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