methyl (2-O-benzoyl-3-O-benzyl-α-L-idopyranosyl)uronate-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranoside | 697795-88-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2-O-benzoyl-3-O-benzyl-α-L-idopyranosyl)uronate-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranoside
• 英文别名: methyl (2R,3S,4S,5R,6R)-6-[[(1R,2S,3R,4R,5R)-4-azido-3-phenylmethoxy-6,8-dioxabicyclo[3.2.1]octan-2-yl]oxy]-5-benzoyloxy-3-hydroxy-4-phenylmethoxyoxane-2-carboxylate
• CAS: 697795-88-3
• 化学式: C₃₄H₃₅N₃O₁₁
• 分子量: 661.665
• InChiKey: WXTCAYDKAIXWLS-MOTMWELJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  48
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  143
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl (2-O-benzoyl-3-O-benzyl-α-L-idopyranosyl)uronate-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 氨 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 methyl (2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-α-L-idopyranosyl)uronate-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-D-glucopyranose
  参考文献：
  名称：

  Toward synthesis of the regular sequence of heparin: synthesis of two tetrasaccharide precursors

  摘要：

  Two fully protected tetrasaccharides, which represent precursors for the synthesis of the regular sequence of heparin, were synthesized via coupling of a pair of disaccharide trichloroacetimidates with a thioglycoside and a glucosamine derivative, respectively, in a sequential manner. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.02.020
• 作为产物：
  描述：

  1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose 在 tetra(n-tert-butyl)ammonium bromide 、 potassium bromide 盐酸 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 calcium hypochlorite 、 4 A molecular sieve 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 6.5h， 生成 methyl (2-O-benzoyl-3-O-benzyl-α-L-idopyranosyl)uronate-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Toward synthesis of the regular sequence of heparin: synthesis of two tetrasaccharide precursors

  摘要：

  Two fully protected tetrasaccharides, which represent precursors for the synthesis of the regular sequence of heparin, were synthesized via coupling of a pair of disaccharide trichloroacetimidates with a thioglycoside and a glucosamine derivative, respectively, in a sequential manner. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.02.020

文献信息

• A facile preparation of uronates via selective oxidation with TEMPO/KBr/Ca(OCl)2 under aqueous conditions
  作者：Feng Lin、Wenjie Peng、Wen Xu、Xiuwen Han、Biao Yu

  DOI：10.1016/j.carres.2004.02.001

  日期：2004.4

  the TEMPO-mediated selective oxidation has the benefit of easier operation. A variety of partially protected saccharide derivatives (1a-l) have been successfully converted into the corresponding uronate derivatives, including disaccharide building blocks for GAG fragments and precursors to saponins. The beneficial effect of Aliquat 336 was also disclosed in the oxidation of certain substrates.

  在TEMPO介导的选择性氧化中添加固体Ca（OCl）（2）作为终端氧化剂具有易于操作的优点。多种部分受保护的糖衍生物（1a-1）已成功转化为相应的尿酸酯衍生物，包括GAG片段的二糖结构单元和皂苷的前体。在某些底物的氧化中也公开了Aliquat 336的有益作用。
• Toward synthesis of the regular sequence of heparin: synthesis of two tetrasaccharide precursors
  作者：Ying Zhou、Feng Lin、Jianfang Chen、Biao Yu

  DOI：10.1016/j.carres.2006.02.020

  日期：2006.7

  Two fully protected tetrasaccharides, which represent precursors for the synthesis of the regular sequence of heparin, were synthesized via coupling of a pair of disaccharide trichloroacetimidates with a thioglycoside and a glucosamine derivative, respectively, in a sequential manner. (c) 2006 Elsevier Ltd. All rights reserved.