(4S)-4-[(benzyloxy)methyl]-1,3-oxazolidin-2-one | 158612-99-8

• 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: (4S)-4-[(benzyloxy)methyl]-1,3-oxazolidin-2-one
• 英文别名: (S)-4-(benzyloxymethyl)oxazolidin-2-one；(4S)-4-[(Benzyloxy)methyl]-1,3-oxazolidin-2-one；(4S)-4-(phenylmethoxymethyl)-1,3-oxazolidin-2-one
• CAS: 158612-99-8
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: QLNHTMVVULBOOR-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S)-4-[(benzyloxy)methyl]-1,3-oxazolidin-2-one 在 sodium tetrahydroborate 、 potassium tert-butylate 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 S-(2-{(4S)-4-[(benzyloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl) ethanethioate
  参考文献：
  名称：

  Synthesis and evaluation of novel modified γ-lactam prostanoids as EP4 subtype-selective agonists

  摘要：

  To identify chemically and metabolically stable subtype-selective EP4 agonists, design and synthesis of a series of modified gamma-lactam prostanoids has been continued. Prostanoids bearing 2-oxo-1,3-oxazolidine, 2-oxo-1,3-thiazolidine and 5-thioxopyrrolidine as a surrogate for the gamma-hydroxycyclopentanone without a troublesome 11-hydroxy group were identified as highly subtype-selective EP4 agonists. Among the tested, several representative compounds demonstrated in vivo efficacy after oral dosing in rats. Their pharmacokinetic and structure-activity relationship studies are presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.009
• 作为产物：
  描述：

  N-(tert-butyloxycarbonyl)-O-benzyl-L-serinol 在 盐酸 、 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 5.5h， 生成 (4S)-4-[(benzyloxy)methyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Synthesis and evaluation of novel modified γ-lactam prostanoids as EP4 subtype-selective agonists

  摘要：

  To identify chemically and metabolically stable subtype-selective EP4 agonists, design and synthesis of a series of modified gamma-lactam prostanoids has been continued. Prostanoids bearing 2-oxo-1,3-oxazolidine, 2-oxo-1,3-thiazolidine and 5-thioxopyrrolidine as a surrogate for the gamma-hydroxycyclopentanone without a troublesome 11-hydroxy group were identified as highly subtype-selective EP4 agonists. Among the tested, several representative compounds demonstrated in vivo efficacy after oral dosing in rats. Their pharmacokinetic and structure-activity relationship studies are presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.009

文献信息

• Synthetic Access to All Four Stereoisomers of Oxetin
  作者：Ahmad F. Kassir、Sherif S. Ragab、Thao A. M. Nguyen、Florence Charnay-Pouget、Régis Guillot、Marie-Christine Scherrmann、Thomas Boddaert、David J. Aitken

  DOI：10.1021/acs.joc.6b01795

  日期：2016.10.21

  3-amino-2-oxetanecarboxylic acid (oxetin) is described. The oxetane core is built using a Paternò–Büchi photochemical [2 + 2] cycloaddition; from the key intermediates, complementary resolution protocols provide access to enantiomerically pure oxetin and epi-oxetin on gram-scale.

  描述了3-氨基-2-氧杂环丁烷羧酸（oxetin）的所有四个立体异构体的简短合成。氧杂环丁烷核心是使用Paternò–Büchi光化学[2 + 2]环加成反应构建的；从关键中间体开始，补充拆分方案可提供对映体纯的oxetin和epi -oxetin的克级分析方法。
• Rearrangements and racemisation during the synthesis of l-serine derived oxazolidin-2-ones
  作者：Sean P Bew、Steven D Bull、Stephen G Davies、Edward D Savory、David J Watkin

  DOI：10.1016/s0040-4020(02)01223-1

  日期：2002.11

  The propensity for N-Boc-4-hydroxymethyl-oxazolidin-2-ones to undergo rapid O-O and N-O carbonyl transfer makes these L-serine derived chiral auxiliaries unsuitable for attachment to polymers. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Polymer supported oxazolidin-2-ones derived from l-serine—a cautionary tale
  作者：Sean P Bew、Steven D Bull、Stephen G Davies

  DOI：10.1016/s0040-4039(00)01301-0

  日期：2000.9

  The capacity of N-Boc-4-hydroxymethyl-oxazolidin-2-ones to undergo rapid O-O and N-O acyl transfer makes these serine derived chiral auxiliaries unsuitable for attachment to polymers. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of the (α,α-difluoroalkyl)phosphonate analogue of phosphoserine
  作者：David B. Berkowitz、Quanrong Shen、Jun-Ho Maeng

  DOI：10.1016/s0040-4039(00)78242-6

  日期：1994.8

  The synthesis of the (alpha,alpha-difluoroalkyl)phosphonate analogue of L-phosphoserine, 5, in a form appropriate for solid phase peptide synthesis, is reported. Two independent routes are described, starting from L-serine or (R)-isopropylideneglycerol. In each case, PCF2-C bond formation is achieved by triflate displacement with diethyl lithiodifluoromethylphosphonate.
• Synthesis and evaluation of novel modified γ-lactam prostanoids as EP4 subtype-selective agonists
  作者：Tohru Kambe、Toru Maruyama、Toshihiko Nagase、Seiji Ogawa、Chiaki Minamoto、Kiyoto Sakata、Takayuki Maruyama、Hisao Nakai、Masaaki Toda

  DOI：10.1016/j.bmc.2011.12.009

  日期：2012.1

  To identify chemically and metabolically stable subtype-selective EP4 agonists, design and synthesis of a series of modified gamma-lactam prostanoids has been continued. Prostanoids bearing 2-oxo-1,3-oxazolidine, 2-oxo-1,3-thiazolidine and 5-thioxopyrrolidine as a surrogate for the gamma-hydroxycyclopentanone without a troublesome 11-hydroxy group were identified as highly subtype-selective EP4 agonists. Among the tested, several representative compounds demonstrated in vivo efficacy after oral dosing in rats. Their pharmacokinetic and structure-activity relationship studies are presented. (C) 2011 Elsevier Ltd. All rights reserved.