(R)-(-)-2-Benzyloxy-<1,1-²H2>propanol | 135416-09-0

• 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-<1,1-²H2>propanol
• 英文别名: (2R)-1,1-dideuterio-2-phenylmethoxypropan-1-ol
• CAS: 135416-09-0
• 化学式: C₁₀H₁₄O₂
• 分子量: 168.204
• InChiKey: BWCRDMRLKBPUTD-VJQDKCMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-(-)-2-Benzyloxy-<1,1-²H2>propanol 在 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 生成 (R)-(-)-Diethyl-(2-benzyloxy-<1,1-²H2>propyl)phosphonat
  参考文献：
  名称：

  Markierte Vertreter eines m�glichen Zwischenprodukts der Biosynthese von Fosfomycin inStreptomyces fradiae: Darstellung von (R,S)-(2-Hydroxypropyl)-, (R,S)-, (R)-, (S)-(2-Hydroxy-[1,1-2H2]propyl)-und (R,S)-(2-[18O]Hydroxypropyl)phosphons�ure

  摘要：

  Racemic methyl O-benzyllactate was reduced to the alcohol, transformed into the bromide and reacted with triethylphosphite to give the diethylphosphonate. Removal of protecting groups afforded a phosphonic acid which was purified as its cyclohexylammonium salt. (S)-Ethyl and (R)-isobutyl O-benzyllactate were reduced with LiAlD4 to the corresponding dideuteriated alcohols, which were transformed in the same way as the racemic compound into the chiral (2-hydroxy-[1,1-H-2(2)]propyl)phosphonic acids. The optical purity of alcohols (S)- and (R)-6b was determined by derivatisation with (+)-MTPA-Cl and H-1-NMR-spectroscopy to be 98%. Exchange of the carbonyl-16-oxygen atom of 2-oxopropylphosphonate for oxygen-18 from (H2O)-O-18, reduction with NaBH4, deprotection and addition of cyclohexylamine yielded the salt (+/-)-18 of (2-[O-18]hydroxy-propyl)phosphonic acid.

  DOI：

  10.1007/bf00809660
• 作为产物：
  描述：

  (R)-(+)-isobutyl O-benzyllactate 在 lithium aluminium deuteride 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到(R)-(-)-2-Benzyloxy-<1,1-²H2>propanol
  参考文献：
  名称：

  Markierte Vertreter eines m�glichen Zwischenprodukts der Biosynthese von Fosfomycin inStreptomyces fradiae: Darstellung von (R,S)-(2-Hydroxypropyl)-, (R,S)-, (R)-, (S)-(2-Hydroxy-[1,1-2H2]propyl)-und (R,S)-(2-[18O]Hydroxypropyl)phosphons�ure

  摘要：

  Racemic methyl O-benzyllactate was reduced to the alcohol, transformed into the bromide and reacted with triethylphosphite to give the diethylphosphonate. Removal of protecting groups afforded a phosphonic acid which was purified as its cyclohexylammonium salt. (S)-Ethyl and (R)-isobutyl O-benzyllactate were reduced with LiAlD4 to the corresponding dideuteriated alcohols, which were transformed in the same way as the racemic compound into the chiral (2-hydroxy-[1,1-H-2(2)]propyl)phosphonic acids. The optical purity of alcohols (S)- and (R)-6b was determined by derivatisation with (+)-MTPA-Cl and H-1-NMR-spectroscopy to be 98%. Exchange of the carbonyl-16-oxygen atom of 2-oxopropylphosphonate for oxygen-18 from (H2O)-O-18, reduction with NaBH4, deprotection and addition of cyclohexylamine yielded the salt (+/-)-18 of (2-[O-18]hydroxy-propyl)phosphonic acid.

  DOI：

  10.1007/bf00809660

文献信息

• HAMMERSCHMIDT, FRIEDRICH, MONATSH. CHEM., 122,(1991) N, C. 389-398
  作者：HAMMERSCHMIDT, FRIEDRICH

  DOI：——

  日期：——