(E)-(S)-4-tert-Butoxycarbonylamino-5-trityloxy-pent-2-enoic acid methyl ester | 126179-16-6

• 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: (E)-(S)-4-tert-Butoxycarbonylamino-5-trityloxy-pent-2-enoic acid methyl ester
• 英文别名: methyl (E,4S)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-trityloxypent-2-enoate
• CAS: 126179-16-6
• 化学式: C₃₀H₃₃NO₅
• 分子量: 487.596
• InChiKey: COWJXBKCVSWQIC-RJOAZTIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-(S)-4-tert-Butoxycarbonylamino-5-trityloxy-pent-2-enoic acid methyl ester 在 potassium osmate(VI) 、 (DHQD)2PHAL 、 甲基磺酰胺 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 反应 12.0h， 以84%的产率得到(2S,3R,4R)-4-tert-Butoxycarbonylamino-2,3-dihydroxy-5-trityloxy-pentanoic acid methyl 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：

  tert-butyl (5S)-2-oxo-3-phenylselanyl-5-(trityloxymethyl)pyrrolidine-1-carboxylate 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 1.25h， 生成 (E)-(S)-4-tert-Butoxycarbonylamino-5-trityloxy-pent-2-enoic acid methyl 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

文献信息

• IKOTA, NOBUO, HETEROCYCLES, 29,(1989) N, C. 1469-1472
  作者：IKOTA, NOBUO

  DOI：——

  日期：——
• 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.