dimethylthexylsilyl 4,6-O-benzylidene-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-β-D-glucopyranoside | 1616628-00-2

• 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: dimethylthexylsilyl 4,6-O-benzylidene-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-β-D-glucopyranoside
• CAS: 1616628-00-2
• 化学式: C₂₈H₄₀Cl₃NO₈Si
• 分子量: 653.072
• InChiKey: OEMZCCFBCQCAGQ-ZYZLCCBESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.62
• 重原子数：
  41.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  109.39
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  dimethylthexylsilyl 4,6-O-benzylidene-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-β-D-glucopyranoside 在 吡啶 、 三乙基硅烷 、 pyridine hydrofluoride 、 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 123.0h， 生成 methyl [3-azidopropyl 2,3-di-O-benzoyl-4-O-(4-O-acetyl-6-O-benzyl-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-glucopyranoside]uronate
  参考文献：
  名称：

  Synthesis of hyaluronic acid oligosaccharides and exploration of a fluorous-assisted approach

  摘要：

  The synthesis of hyaluronic acid oligomers (tri- and tetrasaccharide) is described. We have followed a pre-glycosylation oxidation strategy. Glucuronic acid units were directly employed in coupling reactions with suitably protected glucosamine derivatives. In order to simplify the purification of synthetic intermediates, a fluorous-assisted strategy has been also explored. Using this approach, a hyaluronic acid trisaccharide was prepared. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.05.007
• 作为产物：
  描述：

  Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-hydroxy-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester 在 咪唑 、 甲醇 、 4-二甲氨基吡啶 、 sodium methylate 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 42.0h， 生成 dimethylthexylsilyl 4,6-O-benzylidene-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of hyaluronic acid oligosaccharides and exploration of a fluorous-assisted approach

  摘要：

  The synthesis of hyaluronic acid oligomers (tri- and tetrasaccharide) is described. We have followed a pre-glycosylation oxidation strategy. Glucuronic acid units were directly employed in coupling reactions with suitably protected glucosamine derivatives. In order to simplify the purification of synthetic intermediates, a fluorous-assisted strategy has been also explored. Using this approach, a hyaluronic acid trisaccharide was prepared. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.05.007