(2R)-N-tert-butoxycarbonyl-O-benzyl[1-2H]serinal | 910908-86-0

• 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: (2R)-N-tert-butoxycarbonyl-O-benzyl[1-2H]serinal
• 英文别名: tert-butyl N-[(2R)-1-deuterio-1-oxo-3-phenylmethoxypropan-2-yl]carbamate
• CAS: 910908-86-0
• 化学式: C₁₅H₂₁NO₄
• 分子量: 280.328
• InChiKey: SYUMPFHICOKGEB-VWNAPYERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R)-N-tert-butoxycarbonyl-O-benzyl[1-2H]serinal 在 吡啶 、 4-二甲氨基吡啶 、 (-)-(S)-alpine-borane 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (2R,3R)-N-tert-butoxycarbonyl-O³-acetyl-O¹-benzyl[3-2H]serinol
  参考文献：
  名称：

  Preparation of l-serine and l-cystine stereospecifically labeled with deuterium at the β-position

  摘要：

  The synthesis of L-serine and L-cystine stereospecifically labeled with deuterium at the beta-position is described. The carboxyl group of D-serine was transformed into chirally deuterium-labeled alcohol via asymmetric reduction of 1-deuterio aldehyde, while the original hydroxymethyl group was converted into a carboxyl functionality to afford (2S, 3R)-[3-H-2]serine. Functional group interconversions of the hydroxyl group in the obtained deuterium-labeled L-serine gave (2R, 2'R, 3S, 3'S)-[3, 3'-H-2(2)]cystine. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.039
• 作为产物：
  描述：

  N-Boc-O-苄基-D-丝氨酸 在 lithium aluminium deuteride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 1.0h， 生成 (2R)-N-tert-butoxycarbonyl-O-benzyl[1-2H]serinal
  参考文献：
  名称：

  Preparation of l-serine and l-cystine stereospecifically labeled with deuterium at the β-position

  摘要：

  The synthesis of L-serine and L-cystine stereospecifically labeled with deuterium at the beta-position is described. The carboxyl group of D-serine was transformed into chirally deuterium-labeled alcohol via asymmetric reduction of 1-deuterio aldehyde, while the original hydroxymethyl group was converted into a carboxyl functionality to afford (2S, 3R)-[3-H-2]serine. Functional group interconversions of the hydroxyl group in the obtained deuterium-labeled L-serine gave (2R, 2'R, 3S, 3'S)-[3, 3'-H-2(2)]cystine. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.039

文献信息

• Preparation of l-serine and l-cystine stereospecifically labeled with deuterium at the β-position
  作者：Makoto Oba、Akira Iwasaki、Hiroshi Hitokawa、Toshinori Ikegame、Hiroyuki Banba、Kozo Ura、Tadashi Takamura、Kozaburo Nishiyama

  DOI：10.1016/j.tetasy.2006.06.039

  日期：2006.7

  The synthesis of L-serine and L-cystine stereospecifically labeled with deuterium at the beta-position is described. The carboxyl group of D-serine was transformed into chirally deuterium-labeled alcohol via asymmetric reduction of 1-deuterio aldehyde, while the original hydroxymethyl group was converted into a carboxyl functionality to afford (2S, 3R)-[3-H-2]serine. Functional group interconversions of the hydroxyl group in the obtained deuterium-labeled L-serine gave (2R, 2'R, 3S, 3'S)-[3, 3'-H-2(2)]cystine. (c) 2006 Elsevier Ltd. All rights reserved.