(R)-2-benzyloxy-<1-(2)H1>ethanol | 115463-84-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-benzyloxy-<1-(2)H1>ethanol
• 英文别名: (1R)-1-deuterio-2-phenylmethoxyethanol
• CAS: 115463-84-8
• 化学式: C₉H₁₂O₂
• 分子量: 153.185
• InChiKey: CUZKCNWZBXLAJX-MUFQJMLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (R)-2-benzyloxy-<1-(2)H1>ethanol 生成 (S)-(+)-N-<2-(Benzyloxy)<1-D1>ethyl>phthalimid
  参考文献：
  名称：

  HAMMERSCHMIDT, FRIEDRICH, LIEBIGG ANN. CHEM.,(1988) N 10, C. 961-964

  摘要：

  DOI：
• 作为产物：
  描述：

  (+)-(S)-2-(benzyloxy)(1-2H)ethanol 在 三苯基膦 、 苯甲酸 、 偶氮二甲酸二乙酯 作用下， 生成 (R)-2-benzyloxy-<1-(2)H1>ethanol
  参考文献：
  名称：

  Biosynthesis of natural products with a phosphorus-carbon bond. 7. Synthesis of [1,1-2H2]-, [2,2-2H2]-, (R)- and (S)-[1-2H1](2-hydroxyethyl)phosphonic acid and (R,S)-[1-2H1](1,2-dihydroxyethyl)phosphonic acid and incorporation studies into fosfomycin in Streptomyces fradiae

  摘要：

  Nondeuteriated and deuteriated 2-(benzyloxy)ethanols (8a-c) were transformed into (2-hydroxyethyl)phosphonic acids (12a-c). 8c was prepared from dimethyl 2,3-O-isopropylidene-L-tartrate. 12b,c were fed to Streptomyces fradiae and were incorporated into fosfomycin (2), which was converted to amino phosphonic acid (-)-13. (-)-13 derived from 12b,c contained 42% and 34% deuterium, respectively. (1,2-Dihydroxyethyl)phosphonic acid ((+/-)-29) was not incorporated into fosfomycin. (S)- and (R)-(2-hydroxy[1-H-2-1]ethyl)phosphonic acids ((S)- and (R)-34) were prepared from (S)-2-(benzyloxy)[1-H-2-1]ethanol ((S)-30) and fed to S. fradiae. The deuterium of (R)-34 was lost, and the deuterium of (S)-34 was retained on incorporation into fosfomycin. The optical purity of (S)- and (R)-34 (84% and 86%, respectively) was determined by transformation to dimethyl ester and esterification with (+)-MTPA-Cl to afford 39b,c. 41 obtained from (S)-32 was identical with an authentic sample prepared from (S)-(2-amino[1-H-2-1]ethyl)phosphonic acid.

  DOI：

  10.1021/jo00007a022

文献信息

• Hammerschmidt, Friedrich, Liebigs Annalen der Chemie, 1992, # 6, p. 553 - 558
  作者：Hammerschmidt, Friedrich

  DOI：——

  日期：——
• Convenient Preparation of Chiral Primary Alcohols <i>via</i> Catalytic Asymmetric Reduction of Aldehydes Using Bu₃SnD
  作者：Gary E. Keck、Dhileepkumar Krishnamurthy

  DOI：10.1021/jo961593s

  日期：1996.1.1
• HAMMERSCHMIDT, F.;KAHLIG, HANSPETER, J. ORG. CHEM., 56,(1991) N, C. 2364-2370
  作者：HAMMERSCHMIDT, F.、KAHLIG, HANSPETER

  DOI：——

  日期：——
• HAMMERSCHMIDT, FRIEDRICH, LIEBIGG ANN. CHEM.,(1988) N 10, C. 961-964
  作者：HAMMERSCHMIDT, FRIEDRICH

  DOI：——

  日期：——
• Biosynthesis of natural products with a phosphorus-carbon bond. 7. Synthesis of [1,1-2H2]-, [2,2-2H2]-, (R)- and (S)-[1-2H1](2-hydroxyethyl)phosphonic acid and (R,S)-[1-2H1](1,2-dihydroxyethyl)phosphonic acid and incorporation studies into fosfomycin in Streptomyces fradiae
  作者：Friedrich Hammerschmidt、Hanspeter Kaehlig

  DOI：10.1021/jo00007a022

  日期：1991.3

  Nondeuteriated and deuteriated 2-(benzyloxy)ethanols (8a-c) were transformed into (2-hydroxyethyl)phosphonic acids (12a-c). 8c was prepared from dimethyl 2,3-O-isopropylidene-L-tartrate. 12b,c were fed to Streptomyces fradiae and were incorporated into fosfomycin (2), which was converted to amino phosphonic acid (-)-13. (-)-13 derived from 12b,c contained 42% and 34% deuterium, respectively. (1,2-Dihydroxyethyl)phosphonic acid ((+/-)-29) was not incorporated into fosfomycin. (S)- and (R)-(2-hydroxy[1-H-2-1]ethyl)phosphonic acids ((S)- and (R)-34) were prepared from (S)-2-(benzyloxy)[1-H-2-1]ethanol ((S)-30) and fed to S. fradiae. The deuterium of (R)-34 was lost, and the deuterium of (S)-34 was retained on incorporation into fosfomycin. The optical purity of (S)- and (R)-34 (84% and 86%, respectively) was determined by transformation to dimethyl ester and esterification with (+)-MTPA-Cl to afford 39b,c. 41 obtained from (S)-32 was identical with an authentic sample prepared from (S)-(2-amino[1-H-2-1]ethyl)phosphonic acid.