methyl 2-azido-2-deoxy-3-O-levulinoyl-β-D-glucopyranoside | 473542-36-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: methyl 2-azido-2-deoxy-3-O-levulinoyl-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-5-azido-3-hydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl] 4-oxopentanoate
• CAS: 473542-36-8
• 化学式: C₁₂H₁₉N₃O₇
• 分子量: 317.299
• InChiKey: FRQWYOMOXDYCAQ-YNVCDSSISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 2-azido-2-deoxy-3-O-levulinoyl-β-D-glucopyranoside 在 咪唑 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 乙酸肼 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 methyl 4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Selectively Protected Disaccharide Building Blocks for Modular Synthesis of Heparin Fragments

  摘要：

  A modular approach for the synthesis of heparin fragments is described, Levulinoyl esters were employed to protect those hydroxy groups intended to be sulfated in the final product, while acetyl esters and benzyl ethers were used as the permanent protecting groups. A highly efficient chemoenzymatic reaction sequence was used for the deprotection of an O-sulfated fragment, while the final stage of the synthesis entailed a selective oxidation of a primary alcohol of a glucoside with TENIPO/NaOCl to give a glucuronic acid moiety. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200207)2002:13<2033::aid-ejoc2033>3.0.co;2-w
• 作为产物：
  描述：

  methyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 methyl 2-azido-2-deoxy-3-O-levulinoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Selectively Protected Disaccharide Building Blocks for Modular Synthesis of Heparin Fragments

  摘要：

  A modular approach for the synthesis of heparin fragments is described, Levulinoyl esters were employed to protect those hydroxy groups intended to be sulfated in the final product, while acetyl esters and benzyl ethers were used as the permanent protecting groups. A highly efficient chemoenzymatic reaction sequence was used for the deprotection of an O-sulfated fragment, while the final stage of the synthesis entailed a selective oxidation of a primary alcohol of a glucoside with TENIPO/NaOCl to give a glucuronic acid moiety. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200207)2002:13<2033::aid-ejoc2033>3.0.co;2-w

文献信息

• Selectively Protected Disaccharide Building Blocks for Modular Synthesis of Heparin Fragments
  作者：Michael F. Haller、Geert-Jan Boons

  DOI：10.1002/1099-0690(200207)2002:13<2033::aid-ejoc2033>3.0.co;2-w

  日期：2002.7

  A modular approach for the synthesis of heparin fragments is described, Levulinoyl esters were employed to protect those hydroxy groups intended to be sulfated in the final product, while acetyl esters and benzyl ethers were used as the permanent protecting groups. A highly efficient chemoenzymatic reaction sequence was used for the deprotection of an O-sulfated fragment, while the final stage of the synthesis entailed a selective oxidation of a primary alcohol of a glucoside with TENIPO/NaOCl to give a glucuronic acid moiety. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.