(R)-2-tert-Butoxycarbonylamino-3-[2-((R)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethylsulfanyl)-ethylsulfanyl]-propionic acid methyl ester | 209342-88-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-2-tert-Butoxycarbonylamino-3-[2-((R)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethylsulfanyl)-ethylsulfanyl]-propionic acid methyl ester
• 英文别名: methyl (2R)-3-[2-[(2R)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]sulfanylethylsulfanyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 209342-88-1
• 化学式: C₂₀H₃₆N₂O₈S₂
• 分子量: 496.646
• InChiKey: FBFFHYIDBYCJEG-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  32
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  180
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (R)-2-tert-Butoxycarbonylamino-3-[2-((R)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethylsulfanyl)-ethylsulfanyl]-propionic acid methyl ester 在 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 (4R,11R)-4,11-diamino-3,12-diethyl-6,9-dithia-tetradecan-3,12-diol
  参考文献：
  名称：

  Synthesis of C2-symmetrical bis-β-amino alcohols from (R)-cysteine and their application in enantioselective catalysis

  摘要：

  Six new sulfur-containing C-2-symmetrical bis-beta-primary and sec-amino-tert-alcohols have been synthesized from (R)-cysteine and applied successfully in the enantiocontrolled catalytic addition of diethylzinc to benzaldehyde. The resulting 1-phenyl-1-propanol could be obtained in good enantiomeric excess of up to 94%. Using the same chiral auxiliaries in the enantioselective borane reduction of acetophenone afforded l-phenyl-l-ethanol in enantiomeric excesses of up to 82%. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00106-2
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 (R)-2-Amino-3-[2-((R)-2-amino-2-methoxycarbonyl-ethylsulfanyl)-ethylsulfanyl]-propionic acid methyl ester; hydrochloride 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以93%的产率得到(R)-2-tert-Butoxycarbonylamino-3-[2-((R)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethylsulfanyl)-ethylsulfanyl]-propionic acid methyl ester
  参考文献：
  名称：

  Synthesis of C2-symmetrical bis-β-amino alcohols from (R)-cysteine and their application in enantioselective catalysis

  摘要：

  Six new sulfur-containing C-2-symmetrical bis-beta-primary and sec-amino-tert-alcohols have been synthesized from (R)-cysteine and applied successfully in the enantiocontrolled catalytic addition of diethylzinc to benzaldehyde. The resulting 1-phenyl-1-propanol could be obtained in good enantiomeric excess of up to 94%. Using the same chiral auxiliaries in the enantioselective borane reduction of acetophenone afforded l-phenyl-l-ethanol in enantiomeric excesses of up to 82%. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00106-2

文献信息

• Synthesis of C2-symmetrical bis-β-amino alcohols from (R)-cysteine and their application in enantioselective catalysis
  作者：Michael Kossenjans、Jürgen Martens

  DOI：10.1016/s0957-4166(98)00106-2

  日期：1998.4

  Six new sulfur-containing C-2-symmetrical bis-beta-primary and sec-amino-tert-alcohols have been synthesized from (R)-cysteine and applied successfully in the enantiocontrolled catalytic addition of diethylzinc to benzaldehyde. The resulting 1-phenyl-1-propanol could be obtained in good enantiomeric excess of up to 94%. Using the same chiral auxiliaries in the enantioselective borane reduction of acetophenone afforded l-phenyl-l-ethanol in enantiomeric excesses of up to 82%. (C) 1998 Elsevier Science Ltd. All rights reserved.