(3R,4R,5R,6S)-1,3,4-tri-O-benzyl-1,3,4,5,6-pentahydroxy-2-methylene-oct-7-ene | 1169701-54-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3R,4R,5R,6S)-1,3,4-tri-O-benzyl-1,3,4,5,6-pentahydroxy-2-methylene-oct-7-ene
• 英文别名: (3S,4R,5R,6R)-5,6-bis(phenylmethoxy)-7-(phenylmethoxymethyl)octa-1,7-diene-3,4-diol
• CAS: 1169701-54-5
• 化学式: C₃₀H₃₄O₅
• 分子量: 474.597
• InChiKey: AMNKTBGMZACIHO-MIPYOGIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  35
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4R,5R,6S)-1,3,4-tri-O-benzyl-1,3,4,5,6-pentahydroxy-2-methylene-oct-7-ene 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 甲苯 为溶剂， 反应 0.83h， 以81%的产率得到3,4,6-tri-O-benzyl-5a-carba-α-D-lyxo-hex-5(5a)-enopyranose
  参考文献：
  名称：

  β-Mannosidase and β-hexosaminidase inhibitors: synthesis of 1,2-bis-epi-valienamine and 1-epi-2-acetamido-2-deoxy-valienamine from d-mannose

  摘要：

  A partially protected C-5=C-5a unsaturated carbasugar with alpha-lyxo configuration is synthesised in five steps and 26% overall yield from a known mannose-derived hemiacetal, using ring-closing metathesis as a key step. This carbasugar is converted into valienamine derivatives with beta-lyxo (i.e., corresponding to beta-manno at C-1-C-4), alpha-lyxo (i.e., corresponding to alpha-manno at C-1-C-4) and beta-2-acetamido-2-deoxy-xylo (i.e., corresponding to beta-GlcNAc at C-1-C-4) configurations. This is the first report of the synthesis of the beta-lyxo compound, 1,2-bis-epi-valienamine, which was found to inhibit Cellulomonas fimi beta-mannosidase (CfMan2A) with K(i) 140 mu M. We report the crystal structures of three protected C-5=C-5a unsaturated carbasugars with lyxo configuration. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.016
• 作为产物：
  描述：

  (3R,4S,5R)-1,3,4-tri-O-benzyl-5,6-O-isopropylidene-1,3,4,5,6-pentahydroxy-2-methylene-oct-7-ene 在 盐酸 、 水 、 溶剂黄146 作用下， 反应 1.0h， 以19%的产率得到(3R,4R,5R,6R)-1,3,4-tri-O-benzyl-1,3,4,5,6-pentahydroxy-2-methylene-oct-7-ene
  参考文献：
  名称：

  β-Mannosidase and β-hexosaminidase inhibitors: synthesis of 1,2-bis-epi-valienamine and 1-epi-2-acetamido-2-deoxy-valienamine from d-mannose

  摘要：

  A partially protected C-5=C-5a unsaturated carbasugar with alpha-lyxo configuration is synthesised in five steps and 26% overall yield from a known mannose-derived hemiacetal, using ring-closing metathesis as a key step. This carbasugar is converted into valienamine derivatives with beta-lyxo (i.e., corresponding to beta-manno at C-1-C-4), alpha-lyxo (i.e., corresponding to alpha-manno at C-1-C-4) and beta-2-acetamido-2-deoxy-xylo (i.e., corresponding to beta-GlcNAc at C-1-C-4) configurations. This is the first report of the synthesis of the beta-lyxo compound, 1,2-bis-epi-valienamine, which was found to inhibit Cellulomonas fimi beta-mannosidase (CfMan2A) with K(i) 140 mu M. We report the crystal structures of three protected C-5=C-5a unsaturated carbasugars with lyxo configuration. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.016

文献信息

• β-Mannosidase and β-hexosaminidase inhibitors: synthesis of 1,2-bis-epi-valienamine and 1-epi-2-acetamido-2-deoxy-valienamine from d-mannose
  作者：Clinton Ramstadius、Omid Hekmat、Lars Eriksson、Henrik Stålbrand、Ian Cumpstey

  DOI：10.1016/j.tetasy.2009.02.016

  日期：2009.5

  A partially protected C-5=C-5a unsaturated carbasugar with alpha-lyxo configuration is synthesised in five steps and 26% overall yield from a known mannose-derived hemiacetal, using ring-closing metathesis as a key step. This carbasugar is converted into valienamine derivatives with beta-lyxo (i.e., corresponding to beta-manno at C-1-C-4), alpha-lyxo (i.e., corresponding to alpha-manno at C-1-C-4) and beta-2-acetamido-2-deoxy-xylo (i.e., corresponding to beta-GlcNAc at C-1-C-4) configurations. This is the first report of the synthesis of the beta-lyxo compound, 1,2-bis-epi-valienamine, which was found to inhibit Cellulomonas fimi beta-mannosidase (CfMan2A) with K(i) 140 mu M. We report the crystal structures of three protected C-5=C-5a unsaturated carbasugars with lyxo configuration. (C) 2009 Elsevier Ltd. All rights reserved.