benzyl 3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside | 26922-15-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside
• 英文别名: benzyl 3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside；Benzyl-3-O-benzyl-2-benzyloxycarbonylamino-2-desoxy-α-D-glucopyranose；Benzyl-<2-desoxy-2-benzyloxycarbonylamino-3-O-benzyl-α-D-glucopyranosid>；benzyl N-[(2S,3R,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-2,4-bis(phenylmethoxy)oxan-3-yl]carbamate
• CAS: 26922-15-6
• 化学式: C₂₈H₃₁NO₇
• 分子量: 493.557
• InChiKey: PAHZUJYMRHYZLK-ACFIUOAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl 3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside 在 10% palladium on active carbon 盐酸 、 甲醇 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 以93%的产率得到Benzyl-2-amino-3-O-benzyl-2-desoxy-α-D-glucopyranosid
  参考文献：
  名称：

  Paulsen, Hans; Krogmann, Christof, Liebigs Annalen der Chemie, 1989, p. 1203 - 1214

  摘要：

  DOI：

文献信息

• Synthesis of anN-Acetylated Heparin Pentasaccharide and its anticoagulant activity in comparison with the heparin pentasaccharide with high anti-factor-Xa activity
  作者：Hans Peter Wessel、Ludvik Labler、Thomas B. Tschopp

  DOI：10.1002/hlca.19890720613

  日期：1989.9.20

  The synthesis of tri-N-acetylated heparin pentasaccharide 2 is described. It was assembled from five suitably blocked monosaccharide units (3–7). Glucuronic-acid building block 4 was prepared from glucose by direct Jones oxidation of the 6-O-trityl derivative 18. The resulting acid 16 was esterified to 17 in large mounts using methyl chloroformate/base. Trimethylsilyl bromide proved to be an excellent

  描述了三-N-乙酰化肝素五糖2的合成。它是从5个合适地保护的单糖单元（组装3 - 7）。通过直接琼斯氧化6- O-三苯甲基衍生物18，由葡萄糖制备葡萄糖醛酸构件4。使用氯甲酸甲酯/碱将所得的酸16大批酯化为17。三甲基甲硅烷基溴化物被证明是水解1--1-烯基糖苷的极佳试剂（19 21）。五糖29通过[2 + 2] +1合成获得的糖基化反应提供了非常好的收率。通过1 H-NMR光谱证实了被保护的寡糖的身份。五糖的顺序解块，Ó -sulfation和Ñ -acetylation得到2，其显示出表现出CA。抗凝血活性比五糖1低600倍。
• Synthesis of heparin fragments. A chemical synthesis of the trisaccharide O-(2-deoxy-2-sulfamido-3,6-di-O-sulfo-α-d-glucopyranosyl)-(1→4)-O-(2-O-sulfo-α-l-idopyranosyluronic acid)-(1→4)-2-deoxy-2-sulfamido-6-O-sulfo-d-glucopyranose heptasodium salt
  作者：Jean-Claude Jacquinet、Maurice Petitou、Philippe Duchaussoy、Isidore Lederman、Jean Choay、Giangiacomo Torri、Pierre Sinaÿ

  DOI：10.1016/0008-6215(84)85281-7

  日期：1984.7

  -acetyl-2-azido-4- O -benzyl-2-deoxy-α- d -glucopyranosyl)-(1→4)- O -(methyl 2- O -acetyl-3- O -benzyl-α- l -idopyranosyluronate)-(1→4)-6- O -acetyl-3- O -benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-α- d - glucopyranoside in 88% yield. O -Deacetylation with sodium hydroxide, followed successively by O -sulfation in N,N -dimethylformamide in the presence of sulfur trioxide-trimethylamine complex, catalytic

  摘要首先将已知的3-O-苄基-1,2-O-异亚丙基-α-d-葡萄糖基呋喃糖转化为3-O-苄基-1,2-O-异亚丙基-β-1-基呋喃醛酸甲酯。酸水解，然后乙酰化并用四溴化钛处理，得到（2,4-二-O-乙酰基-3-O-苄基-α-1-吡喃吡喃基溴化）甲基脲酸酯，其立即被转化为4-O-甲基。乙酰基-3-O-苄基-β-1-氨基吡喃二酸酯1,2-（原乙酸叔丁酯）。用4-O-氯乙酰基进行两步取代4-O-乙酰基得到关键的衍生物结晶结晶3-O-苄基-4-O-氯乙酰基-β-1-氨基吡喃醛酸酯1,2-（叔-原乙酸正丁酯）。该原酸酯与过量的苄基6-O-乙酰基-3-O-苄基-2-（苄氧基羰基）氨基-2-脱氧-α-d-吡喃葡萄糖苷结晶在氯苯存在下缩合2，6-二甲基吡啶鎓高氯酸盐得到结晶的苄基6-O-乙酰基-3-O-苄基-2-（苄氧基羰基）氨基-2-脱氧-4-O-（甲基2-O-乙酰基-3-O-苄基-4- O-氯乙酰基-
• Total synthesis of a heparin pentasaccharide fragment having high affinity for antithrombin III
  作者：Pierre Sinaÿ、Jean-Claude Jacquinet、Maurice Petitou、Philippe Duchaussoy、Isidore Lederman、Jean Choay、Giangiacomo Torri

  DOI：10.1016/0008-6215(84)85236-2

  日期：1984.9
• Selectively O-acylated glycosaminoglycan derivatives
  作者：Maurice Petitou、Catherine Coudert、Michel Level、Jean-Claude Lormeau、Martin Zuber、Catherine Simenel、Jean-Paul Fournier、Jean Choay

  DOI：10.1016/0008-6215(92)85010-w

  日期：1992.12

  Glycosaminoglycans, particularly heparin and heparin fragments, were specifically O-acetylated by use of tetrabutylammonium or tributylammonium salts of the anionic polysaccharides, carboxylic acid anhydrides, and 4-dimethylaminopyridine in an homogeneous way in N,N-dimethylformamide. The number of acyl chains introduced on the carbohydrate backbone was determined either after transesterification and quantitative analysis of the butyl esters thus obtained by GLC or by H-1 NMR spectroscopy.
• Paulsen, Hans; Hayauchi, Yutaka; Unger, Frank M., Liebigs Annalen der Chemie, 1984, # 7, p. 1288 - 1297
  作者：Paulsen, Hans、Hayauchi, Yutaka、Unger, Frank M.

  DOI：——

  日期：——