Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester | 110236-57-2

• 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 (2S,3R,4S,5R,6S)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester
• CAS: 110236-57-2
• 化学式: C₄₈H₅₅NO₁₅
• 分子量: 885.962
• InChiKey: MNHVHLXTBFWOHB-DGLJPYLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.58
• 重原子数：
  64.0
• 可旋转键数：
  20.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  181.84
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以92%的产率得到Methyl-3,6-di-O-benzyl-4-O-(3-O-benzyl-α-L-idopyranosyl)-2-(benzyloxycarbonylamino)-2-desoxy-α-D-glucopyranosid
  参考文献：
  名称：

  Paulsen, Hans; Huffziger, Axel; Boeckel, Constant A. A. van, Liebigs Annalen der Chemie, 1988, p. 419 - 426

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 4,6-O-benzylidene-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside 在 盐酸 、 barium dihydroxide 、 tin(II) trifluoromethanesulfonate 、 sodium cyanoborohydride 、 barium(II) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis of heparin partial structures and their binding activities to platelets

  摘要：

  A synthetic pentasaccharide corresponding to the antithrombin III-binding region in heparin was also found to bind to human platelets. To identify the platelet-binding site in the pentasaccharide which is expected to be a novel sequence in heparin responsible for its platelet-binding, five partial structures of this particular pentasaccharide were synthesized. In a competitive assay using [H-3]-heparin, a trisaccharide, O-(2-deoxy-2-sulfamido-3,6-di-O-sulfo-alpha-D-glucopyranosyl)-(1-->4)-O-(2-O-sulfo-alpha-L-idopyranosyluronic acid)-(1-->4)-2-deoxy-2-sulfamido-6-O-sulfo-alpha-D-glucopyranose, was concluded to be a high-affinity site for heparin's binding to platelets. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00550-8

文献信息

• Synthesis of an antithrombin binding heparin-like pentasaccharide lacking 6-0 sulphate at its reducing end.
  作者：T Beetz、C.A.A van Boeckel

  DOI：10.1016/s0040-4039(00)85356-3

  日期：1986.1