(3S,4S,5R)-3-Amino-1-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-nonadecane-4,5-diol | 793733-72-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4S,5R)-3-Amino-1-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-nonadecane-4,5-diol
• 英文别名: (3S,4S,5R)-3-amino-1-[(2S,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]nonadecane-4,5-diol
• CAS: 793733-72-9
• 化学式: C₅₃H₇₅NO₇
• 分子量: 838.181
• InChiKey: BEZLNXSOQBQWSA-KWIMJMTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  61
• 可旋转键数：
  31
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3S,4S,5R)-3-Amino-1-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-nonadecane-4,5-diol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 氯仿 为溶剂， 生成 Hexacosanoic acid {(1S,2S,3R)-2,3-dihydroxy-1-[2-((2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-ethyl]-heptadecyl}-amide
  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 在 Grubbs catalyst first generation 4-二甲氨基吡啶 、 四氧化锇 、 四甲基乙二胺 、 2-氯-N-(2-氯乙基)-N-甲基乙胺氧化物 、 四氯化钛 、 sodium hydride 、 对甲苯磺酸 、 乙酰氯 、 N,N'-二环己基碳二亚胺 、 lead(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 (3S,4S,5R)-3-Amino-1-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-nonadecane-4,5-diol
  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.