(2S,3R)-3-(tert-butoxycarbonylamino)-1,2-O-isopropylidene-1,2-butanediol | 192764-32-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R)-3-(tert-butoxycarbonylamino)-1,2-O-isopropylidene-1,2-butanediol
• 英文别名: tert-butyl N-[(1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl]carbamate
• CAS: 192764-32-2
• 化学式: C₁₂H₂₃NO₄
• 分子量: 245.319
• InChiKey: QYLOHMMLBJJYII-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  56.79
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-(tert-butoxycarbonylamino)-1,2-O-isopropylidene-1,2-butanediol 在 咪唑 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 [(1R,2S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-1-methyl-propyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Stereocontrolled addition of Grignard reagents to α-alkoxy nitrones. Synthesis of syn and anti 3-amino-1,2-diols

  摘要：

  The stereoselective addition of Grignard reagents to alpha-alkoxy nitrones has been achieved with excellent stereocontrol using ZnBr2 and Et2AlCl as precomplexing agents to obtain the corresponding syn- and anti- adducts, respectively. The obtained hydroxylamines have been transformed into valuable 3-amino-1,2-diols. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00175-4
• 作为产物：
  描述：

  N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone 在 palladium dihydroxide 氢气 、 zinc dibromide 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， -40.0~25.0 ℃ 、482.63 kPa 条件下， 反应 94.0h， 生成 (2S,3R)-3-(tert-butoxycarbonylamino)-1,2-O-isopropylidene-1,2-butanediol
  参考文献：
  名称：

  Stereocontrolled addition of Grignard reagents to α-alkoxy nitrones. Synthesis of syn and anti 3-amino-1,2-diols

  摘要：

  The stereoselective addition of Grignard reagents to alpha-alkoxy nitrones has been achieved with excellent stereocontrol using ZnBr2 and Et2AlCl as precomplexing agents to obtain the corresponding syn- and anti- adducts, respectively. The obtained hydroxylamines have been transformed into valuable 3-amino-1,2-diols. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00175-4

文献信息

• Nucleophilic additions of Grignard reagents to N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (BIGN). Synthesis of (2S,3R) and (2S,3S)-3-phenylisoserine
  作者：Pedro Merino、Elena Castillo、Santiago Franco、Francisco L. Merchán、Tomas Tejero

  DOI：10.1016/s0040-4020(98)00741-8

  日期：1998.10

  A remarkable Lewis acid tuning has been observed in the nucleophilic addition of Grignard reagent to BIGN, the N-benzyl nitrone derived from 1,2-O-isopropylidene-D-glyceraldehyde. The obtained alpha,beta-dialkoxy hydroxylamines can serve as starting points for the synthesis of both aminodiols and alpha-hydroxy-beta-amino acids. This synthetic approach is illustrated by the synthesis of the antipode of the C-13 side chain of Taxotere as well as its C-3 epimer. (C) 1998 Elsevier Science Ltd. All rights reserved.