(S)-4-benzyloxymethyl-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester | 312736-43-9

• 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: (S)-4-benzyloxymethyl-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4S)-2-oxo-4-(phenylmethoxymethyl)-1,3-oxazolidine-3-carboxylate
• CAS: 312736-43-9
• 化学式: C₁₆H₂₁NO₅
• 分子量: 307.346
• InChiKey: JUJFNQRZQYESKH-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-4-benzyloxymethyl-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以82%的产率得到(S)-4-hydroxymethyl-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Rearrangements and racemisation during the synthesis of l-serine derived oxazolidin-2-ones

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(02)01223-1
• 作为产物：
  描述：

  O-苄基-L-丝氨酸 在 4-二甲氨基吡啶 、 dimethyl sulfide borane 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 (S)-4-benzyloxymethyl-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Rearrangements and racemisation during the synthesis of l-serine derived oxazolidin-2-ones

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(02)01223-1

文献信息

• 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.
• 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.