{(R)-Furan-2-yl-[(4S,5S)-5-((S)-5-hydroxy-1-methyl-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methyl}-carbamic acid tert-butyl ester | 190712-28-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: {(R)-Furan-2-yl-[(4S,5S)-5-((S)-5-hydroxy-1-methyl-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methyl}-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(R)-furan-2-yl-[(4S,5S)-5-[(2S)-6-hydroxyhexan-2-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]carbamate
• CAS: 190712-28-8
• 化学式: C₂₁H₃₅NO₆
• 分子量: 397.512
• InChiKey: DXPRQYIBEVYFLP-DKIMLUQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  90.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  {(R)-Furan-2-yl-[(4S,5S)-5-((S)-5-hydroxy-1-methyl-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methyl}-carbamic acid tert-butyl ester 在 咪唑 、 ruthenium(IV) oxide 、 sodium periodate 、 potassium hydrogencarbonate 作用下， 以 四氯化碳 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 40.0h， 生成 (R)-tert-Butoxycarbonylamino-{(4S,5S)-5-[(S)-5-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pentyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-acetic acid methyl ester
  参考文献：
  名称：

  Sunthetic Studies of Microsclerodermins. A Stereoselective Synthesis of a Core Building Block for (2 S,3 R, 4 S,5 S,6 S, 11 E)-3-Amino-6-methyl-12-(4-methoxyphenyl)-2,4,5-trihydroxydodec-11-enoic Acid (AMMTD)

  摘要：

  A core building block 3 for (2S,3R,4S,5S,6S,11E)-3-aminod-methyl-12-(4-methoxyphenyl)-2,4,5-trihydroxydoda. -11-enoic acid (2, AMMTD) has been efficiently synthesized using the sharpless asymmetric dihydroxylation and the Dondoni's furan addition to a nitrone derivative as key steps. The 2-furyl group has been used as the carboxylsynthon. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00522-4
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 sodium 作用下， 以 1,4-二氧六环 、 氨 为溶剂， 反应 18.0h， 生成 {(R)-Furan-2-yl-[(4S,5S)-5-((S)-5-hydroxy-1-methyl-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Sunthetic Studies of Microsclerodermins. A Stereoselective Synthesis of a Core Building Block for (2 S,3 R, 4 S,5 S,6 S, 11 E)-3-Amino-6-methyl-12-(4-methoxyphenyl)-2,4,5-trihydroxydodec-11-enoic Acid (AMMTD)

  摘要：

  A core building block 3 for (2S,3R,4S,5S,6S,11E)-3-aminod-methyl-12-(4-methoxyphenyl)-2,4,5-trihydroxydoda. -11-enoic acid (2, AMMTD) has been efficiently synthesized using the sharpless asymmetric dihydroxylation and the Dondoni's furan addition to a nitrone derivative as key steps. The 2-furyl group has been used as the carboxylsynthon. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00522-4

文献信息

• Sunthetic Studies of Microsclerodermins. A Stereoselective Synthesis of a Core Building Block for (2 S,3 R, 4 S,5 S,6 S, 11 E)-3-Amino-6-methyl-12-(4-methoxyphenyl)-2,4,5-trihydroxydodec-11-enoic Acid (AMMTD)
  作者：Shigekazu Sasaki、Yasumasa Hamada、Takayuki Shioiri*

  DOI：10.1016/s0040-4039(97)00522-4

  日期：1997.4

  A core building block 3 for (2S,3R,4S,5S,6S,11E)-3-aminod-methyl-12-(4-methoxyphenyl)-2,4,5-trihydroxydoda. -11-enoic acid (2, AMMTD) has been efficiently synthesized using the sharpless asymmetric dihydroxylation and the Dondoni's furan addition to a nitrone derivative as key steps. The 2-furyl group has been used as the carboxylsynthon. (C) 1997 Elsevier Science Ltd.