3-(benzyloxycarbonylamino)tetrahydrothiophene-3-carboxylic acid (R)-2′-hydroxy-[1,1′]-binaphthyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(benzyloxycarbonylamino)tetrahydrothiophene-3-carboxylic acid (R)-2′-hydroxy-[1,1′]-binaphthyl ester
• 英文别名: [1-(2-hydroxynaphthalen-1-yl)naphthalen-2-yl] (3R)-3-(phenylmethoxycarbonylamino)thiolane-3-carboxylate
• 化学式: C₃₃H₂₇NO₅S
• 分子量: 549.647
• InChiKey: QZEUOKFSWVPINZ-XIFFEERXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(benzyloxycarbonylamino)tetrahydrothiophene-3-carboxylic acid (R)-2′-hydroxy-[1,1′]-binaphthyl ester 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以95%的产率得到(R)-3-(benzyloxycarbonylamino)tetrahydrothiophene-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of both enantiomers of cyclic methionine analogue: (R)- and (S)-3-aminotetrahydrothiophene-3-carboxylic acids

  摘要：

  A method of synthesizing an optically active cyclic methionine analogue, 3-aminotetrahydrothiophene-3-carboxylic acid (At(5)c), is described. A Bucherer-Bergs reaction of 4,5-dihydro-3(2H)-thiophenone and the subsequent alkaline hydrolysis of a hydantoin, followed by Cbz protection of the amine, afforded racemic Cbz-At(5)c (+/-)-3 in excellent yield. Diastereomeric esters derived from Cbz-At(5)c (+/-)-3 and (R)-BINOL could be separated by column chromatography to give both diastereomers with >99% de. X-ray crystallographic analysis revealed the absolute configuration of the synthesized amino acid derived from the less polar diastereomeric ester to be (S). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.03.010
• 作为产物：
  描述：

  7-thia-1,3-diazaspiro[4.4]nonane-2,4-dione 在 4-二甲氨基吡啶 、 sodium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 192.0h， 生成 3-(benzyloxycarbonylamino)tetrahydrothiophene-3-carboxylic acid (R)-2′-hydroxy-[1,1′]-binaphthyl ester
  参考文献：
  名称：

  Synthesis of both enantiomers of cyclic methionine analogue: (R)- and (S)-3-aminotetrahydrothiophene-3-carboxylic acids

  摘要：

  A method of synthesizing an optically active cyclic methionine analogue, 3-aminotetrahydrothiophene-3-carboxylic acid (At(5)c), is described. A Bucherer-Bergs reaction of 4,5-dihydro-3(2H)-thiophenone and the subsequent alkaline hydrolysis of a hydantoin, followed by Cbz protection of the amine, afforded racemic Cbz-At(5)c (+/-)-3 in excellent yield. Diastereomeric esters derived from Cbz-At(5)c (+/-)-3 and (R)-BINOL could be separated by column chromatography to give both diastereomers with >99% de. X-ray crystallographic analysis revealed the absolute configuration of the synthesized amino acid derived from the less polar diastereomeric ester to be (S). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.03.010

文献信息

• Synthesis of both enantiomers of cyclic methionine analogue: (R)- and (S)-3-aminotetrahydrothiophene-3-carboxylic acids
  作者：Makoto Oba、Atsushi Shimabukuro、Miyako Ono、Mitsunobu Doi、Masakazu Tanaka

  DOI：10.1016/j.tetasy.2013.03.010

  日期：2013.4

  A method of synthesizing an optically active cyclic methionine analogue, 3-aminotetrahydrothiophene-3-carboxylic acid (At(5)c), is described. A Bucherer-Bergs reaction of 4,5-dihydro-3(2H)-thiophenone and the subsequent alkaline hydrolysis of a hydantoin, followed by Cbz protection of the amine, afforded racemic Cbz-At(5)c (+/-)-3 in excellent yield. Diastereomeric esters derived from Cbz-At(5)c (+/-)-3 and (R)-BINOL could be separated by column chromatography to give both diastereomers with >99% de. X-ray crystallographic analysis revealed the absolute configuration of the synthesized amino acid derived from the less polar diastereomeric ester to be (S). (C) 2013 Elsevier Ltd. All rights reserved.