6-O-acetyl-2-azido-1-O-Benzyl-2-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-β-L-gulopyranoside | 1392067-38-7

• 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: 6-O-acetyl-2-azido-1-O-Benzyl-2-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-β-L-gulopyranoside
• 英文别名: [(2S,3S,4aR,5S,6S,8S,8aR)-5-azido-2,3-dimethoxy-2,3-dimethyl-6-phenylmethoxy-4a,5,6,7,8,8a-hexahydrobenzo[b][1,4]dioxin-8-yl]methyl acetate
• CAS: 1392067-38-7
• 化学式: C₂₂H₃₁N₃O₇
• 分子量: 449.504
• InChiKey: FOMYRSHLTYGAQO-LRUMIOPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  86.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6-O-acetyl-2-azido-1-O-Benzyl-2-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-β-L-gulopyranoside 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Syntheses of Carbocyclic Analogues of α-d-Glucosamine, α-d-Mannose, α-d-Mannuronic Acid, β-l-Idosamine, and β-l-Gulose

  摘要：

  A versatile synthesis of orthogonally protected derivatives of carba-alpha-D-glucosamine, carba-alpha-D-mannose, carba-alpha-D-mannuronic acid, carba-beta-L-idosamine, and carba-beta-L-gulose from methyl alpha-D-mannoside is described. Our synthetic strategy utilizes the palladium-promoted Ferrier carbocyclization and persistent butane-2,3-diacetal protection to produce a key chiral cyclohexanone intermediate, from which all five carbasugar derivatives can readily be obtained.

  DOI：

  10.1021/jo301240j
• 作为产物：
  描述：

  methyl (2'S,3'S)-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-α-D-mannoside 在 吡啶 、 咪唑 、 (1S)-(+)-樟脑-10-磺酸,一水合物 、 potassium tert-butylate 、 双氧水 、 碘 、 sodium hydride 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium hydroxide 、 palladium dichloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 64.34h， 生成 6-O-acetyl-2-azido-1-O-Benzyl-2-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-β-L-gulopyranoside
  参考文献：
  名称：

  Syntheses of Carbocyclic Analogues of α-d-Glucosamine, α-d-Mannose, α-d-Mannuronic Acid, β-l-Idosamine, and β-l-Gulose

  摘要：

  A versatile synthesis of orthogonally protected derivatives of carba-alpha-D-glucosamine, carba-alpha-D-mannose, carba-alpha-D-mannuronic acid, carba-beta-L-idosamine, and carba-beta-L-gulose from methyl alpha-D-mannoside is described. Our synthetic strategy utilizes the palladium-promoted Ferrier carbocyclization and persistent butane-2,3-diacetal protection to produce a key chiral cyclohexanone intermediate, from which all five carbasugar derivatives can readily be obtained.

  DOI：

  10.1021/jo301240j

文献信息

• Syntheses of Carbocyclic Analogues of α-<scp>d</scp>-Glucosamine, α-<scp>d</scp>-Mannose, α-<scp>d</scp>-Mannuronic Acid, β-<scp>l</scp>-Idosamine, and β-<scp>l</scp>-Gulose
  作者：Yunshan Sun、Mark Nitz

  DOI：10.1021/jo301240j

  日期：2012.9.7

  A versatile synthesis of orthogonally protected derivatives of carba-alpha-D-glucosamine, carba-alpha-D-mannose, carba-alpha-D-mannuronic acid, carba-beta-L-idosamine, and carba-beta-L-gulose from methyl alpha-D-mannoside is described. Our synthetic strategy utilizes the palladium-promoted Ferrier carbocyclization and persistent butane-2,3-diacetal protection to produce a key chiral cyclohexanone intermediate, from which all five carbasugar derivatives can readily be obtained.