((E)-(S)-1-Hydroxymethyl-2-oxo-heptadec-3-enyl)-(4-methoxy-benzyl)-carbamic acid tert-butyl ester | 231291-93-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ((E)-(S)-1-Hydroxymethyl-2-oxo-heptadec-3-enyl)-(4-methoxy-benzyl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(E,2S)-1-hydroxy-3-oxooctadec-4-en-2-yl]-N-[(4-methoxyphenyl)methyl]carbamate
• CAS: 231291-93-3
• 化学式: C₃₁H₅₁NO₅
• 分子量: 517.75
• InChiKey: XNRJPRWHDIAUNV-YZHQAQFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  37
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ((E)-(S)-1-Hydroxymethyl-2-oxo-heptadec-3-enyl)-(4-methoxy-benzyl)-carbamic acid tert-butyl ester 在 盐酸 、 sodium tetrahydroborate 、 ammonium cerium(IV) nitrate 作用下， 以 甲醇 为溶剂， 生成 L-threo-sphingosine-N,O,O-triacetate
  参考文献：
  名称：

  Stereoselective synthesis of β-amino alcohols: practical preparation of all four stereomers of N-PMB-protected sphingosine from l- and d-serine

  摘要：

  Serine was efficiently converted to the N-p-methoxybenzyl (PMB) protected alpha'-amino enone derivative 6, which was reduced with Zn(BH4)(2) to the corresponding anti-beta-amino alcohol in >96% de. On the other hand, N-PMB-N-Boc-protected alpha'-amino enone derivative 8 was reduced by NaBH4 to syn-product with a diastereoselectivity of ca. 90%. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00147-0
• 作为产物：
  描述：

  肉豆蔻醛 在 盐酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 生成 ((E)-(S)-1-Hydroxymethyl-2-oxo-heptadec-3-enyl)-(4-methoxy-benzyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective synthesis of β-amino alcohols: practical preparation of all four stereomers of N-PMB-protected sphingosine from l- and d-serine

  摘要：

  Serine was efficiently converted to the N-p-methoxybenzyl (PMB) protected alpha'-amino enone derivative 6, which was reduced with Zn(BH4)(2) to the corresponding anti-beta-amino alcohol in >96% de. On the other hand, N-PMB-N-Boc-protected alpha'-amino enone derivative 8 was reduced by NaBH4 to syn-product with a diastereoselectivity of ca. 90%. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00147-0

文献信息

• Stereoselective synthesis of β-amino alcohols: practical preparation of all four stereomers of N-PMB-protected sphingosine from l- and d-serine
  作者：Sung-Kee Chung、Jae-Mok Lee

  DOI：10.1016/s0957-4166(99)00147-0

  日期：1999.4

  Serine was efficiently converted to the N-p-methoxybenzyl (PMB) protected alpha'-amino enone derivative 6, which was reduced with Zn(BH4)(2) to the corresponding anti-beta-amino alcohol in >96% de. On the other hand, N-PMB-N-Boc-protected alpha'-amino enone derivative 8 was reduced by NaBH4 to syn-product with a diastereoselectivity of ca. 90%. (C) 1999 Elsevier Science Ltd. All rights reserved.