Acetic acid (3R,4R,5S,6R)-6-acetoxymethyl-5-allyloxy-3-azido-4-benzyloxy-tetrahydro-pyran-2-yl ester | 241129-82-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (3R,4R,5S,6R)-6-acetoxymethyl-5-allyloxy-3-azido-4-benzyloxy-tetrahydro-pyran-2-yl ester
• 英文别名: [(2R,3S,4R,5R)-6-acetyloxy-5-azido-4-phenylmethoxy-3-prop-2-enoxyoxan-2-yl]methyl acetate
• CAS: 241129-82-8
• 化学式: C₂₀H₂₅N₃O₇
• 分子量: 419.434
• InChiKey: JTPYVJSEKIEZQG-MGXUXCEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  94.6
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Acetic acid (3R,4R,5S,6R)-6-acetoxymethyl-5-allyloxy-3-azido-4-benzyloxy-tetrahydro-pyran-2-yl ester 在 sodium methylate 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 、 苄胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 4-O-allyl-2-azido-3-O-benzyl-2-deoxy-D-glucopyranosyl fluoride
  参考文献：
  名称：

  Convergent synthesis of an inner core GPI of sperm CD52

  摘要：

  An inner core of the GPI anchor of sperm CD52 antigens was synthesized by a highly convergent process using specially modified inositol, glucosamine and phospholipid as key building blocks. This paper also presents a new and efficient procedure to prepare 1,2,6-differentiated derivatives of inositol for GPI syntheses. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00301-3
• 作为产物：
  描述：

  4-O-Allyl-1,6-anhydro-2-O-tosyl-β-D-glucopyranose 在 叠氮化锂 、 sodium methylate 、 sodium hydride 、 氯化铵 、 三氟乙酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 Acetic acid (3R,4R,5S,6R)-6-acetoxymethyl-5-allyloxy-3-azido-4-benzyloxy-tetrahydro-pyran-2-yl ester
  参考文献：
  名称：

  Synthesis and biological activity of oligomer-model compounds containing units of a key platelet-binding disaccharide of heparin

  摘要：

  A key disaccharide unit in heparin, O-(2-deoxy-2-sulfamido-6-O-sulfo-alpha-D-glucopyranosyl)-(1-->4)-2-O-sulfo-alpha-L-idopyranosyluronic acid, was previously found to be responsible for the binding interaction of heparin to platelets. A clustering effect to enhance the binding was found to be dependent on the number and frequency of the disaccharide units in a heparin molecule. To systematically examine the clustering effect, three oligomer-model compounds containing two or three units of the disaccharide were synthesized. These compounds inhibited (3)H-Iabelled heparin binding to human platelets more strongly than a compound containing only one unit of the disaccharide, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01084-9