(S)-4-tert-Butoxycarbonylamino-4-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-butyric acid | 793733-66-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-4-tert-Butoxycarbonylamino-4-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-butyric acid
• 英文别名: (4S)-4-[(4S,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl]-4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid
• CAS: 793733-66-1
• 化学式: C₂₈H₅₃NO₆
• 分子量: 499.732
• InChiKey: NNPMKZNCLZOWLS-ARNLJNQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  35
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-1,3,4-tris(benzyloxy)hex-5-en-2-ol 、 (S)-4-tert-Butoxycarbonylamino-4-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-butyric acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以88%的产率得到(S)-4-tert-Butoxycarbonylamino-4-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-butyric acid (1R,2R,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester
  参考文献：
  名称：

  Synthesis and anti-tumor activity of β-C-glycoside analogs of the immunostimulant KRN7000

  摘要：

  A ring-closing metathesis approach was employed for the synthesis of a beta-C-glycoside analog of the immunostimulant KRN7000. The protected Gglycosyl amino acid derivative 18 was converted to amino-olefin 20, and osmylation served to install the diol unit as a mixture of separable syn and anti isomers. Deprotection to the hydroxy-amine 21 was followed by N-acylation and debenzylation to deliver the target compound 5. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.07.163
• 作为产物：
  描述：

  (S)-4-叔丁氧羰基氨基-5-羟基戊酸甲酯 在 lithium hydroxide 、 四氧化锇 、 2-氯-N-(2-氯乙基)-N-甲基乙胺氧化物 、 camphor-10-sulfonic acid 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 生成 (S)-4-tert-Butoxycarbonylamino-4-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-butyric acid
  参考文献：
  名称：

  Synthesis and anti-tumor activity of β-C-glycoside analogs of the immunostimulant KRN7000

  摘要：

  A ring-closing metathesis approach was employed for the synthesis of a beta-C-glycoside analog of the immunostimulant KRN7000. The protected Gglycosyl amino acid derivative 18 was converted to amino-olefin 20, and osmylation served to install the diol unit as a mixture of separable syn and anti isomers. Deprotection to the hydroxy-amine 21 was followed by N-acylation and debenzylation to deliver the target compound 5. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.07.163

文献信息

• Synthesis and anti-tumor activity of β-C-glycoside analogs of the immunostimulant KRN7000
  作者：Mani Raj Chaulagain、Maarten H.D. Postema、Fred Valeriote、Halina Pietraszkewicz

  DOI：10.1016/j.tetlet.2004.07.163

  日期：2004.10

  A ring-closing metathesis approach was employed for the synthesis of a beta-C-glycoside analog of the immunostimulant KRN7000. The protected Gglycosyl amino acid derivative 18 was converted to amino-olefin 20, and osmylation served to install the diol unit as a mixture of separable syn and anti isomers. Deprotection to the hydroxy-amine 21 was followed by N-acylation and debenzylation to deliver the target compound 5. (C) 2004 Elsevier Ltd. All rights reserved.