(S)-4-[2-((1R,2R,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxycarbonyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester | 793733-68-3

• 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-[2-((1R,2R,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxycarbonyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4S)-2,2-dimethyl-4-[3-oxo-3-[(2R,3R,4R)-1,3,4-tris(phenylmethoxy)hex-5-en-2-yl]oxypropyl]-1,3-oxazolidine-3-carboxylate
• CAS: 793733-68-3
• 化学式: C₄₀H₅₁NO₈
• 分子量: 673.847
• InChiKey: FTZJNNRCLOACHS-ADFXPUFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  49
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  92.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-4-[2-((1R,2R,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxycarbonyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 Grubbs catalyst first generation 四甲基乙二胺 、 四氯化钛 、 sodium hydride 、 lead(II) chloride 作用下， 生成 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-decitol
  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：

  (4S)-4-(2'-carboxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 、 (2R,3S,4R)-1,3,4-tris(benzyloxy)hex-5-en-2-ol 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-[2-((1R,2R,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxycarbonyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl 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

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.