(1S,2S,3S,4S,5S,7S)-7-benzyloxy-4,5-dihydroxy-5-methoxy-2-methoxycarbonyl-6-oxo-4,5-O-(diphenylmethylidene)bicyclo[2.2.2]octan-3-yl 2-acetamido-3,4,6-tri-O-acetyl-1,2-dideoxy-1-thio-β-D-glucopyranoside | 1338920-53-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (1S,2S,3S,4S,5S,7S)-7-benzyloxy-4,5-dihydroxy-5-methoxy-2-methoxycarbonyl-6-oxo-4,5-O-(diphenylmethylidene)bicyclo[2.2.2]octan-3-yl 2-acetamido-3,4,6-tri-O-acetyl-1,2-dideoxy-1-thio-β-D-glucopyranoside
• 英文别名: methyl (1S,5S,7S,8S,9S,11S)-9-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanyl-5-methoxy-6-oxo-3,3-diphenyl-11-phenylmethoxy-2,4-dioxatricyclo[5.2.2.01,5]undecane-8-carboxylate
• CAS: 1338920-53-8
• 化学式: C₄₅H₄₉NO₁₅S
• 分子量: 875.948
• InChiKey: QKOHHKHSIZBYIT-IVLXBHJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  62
• 可旋转键数：
  18
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  223
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  (1S,2S,3S,4S,5S,7S)-7-benzyloxy-4,5-dihydroxy-5-methoxy-2-methoxycarbonyl-6-oxo-4,5-O-(diphenylmethylidene)bicyclo[2.2.2]octan-3-yl 2-acetamido-3,4,6-tri-O-acetyl-1,2-dideoxy-1-thio-β-D-glucopyranoside 在 甲醇 、 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 、 palladium 10% on activated carbon 、 氢气 、 sodium methylate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 30.83h， 生成 (1S,2R,3S,4S,5S,6S,7S)-4,5,6,7-tetrahydroxy-2-methoxycarbonyl-bicyclo[2.2.2]octan-3-yl 2-acetamido-1,2-dideoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis, structural, and biological studies on a pseudodisaccharide containing a bicyclic, bridged carba-sugar

  摘要：

  Two carba-sugar containing pseudodisaccharide diastereomers have been synthesized from a racemic bicyclooctene derivative. The determination of the absolute configurations was carried out by means of CD measurements, CD calculations and X-ray diffraction. The compounds showed moderate competitive inhibitory effects on chondroitin AC-I lyase. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.07.023
• 作为产物：
  描述：

  2-乙酰氨基-2-脱氧-1-硫代-beta-D-吡喃葡萄糖 3,4,6-三乙酸酯 、 methyl 7-benzyloxy-4,5-dihydroxy-5-methoxy-6-oxo-4,5-O-diphenylmethylidenebicyclo[2.2.2]oct-2-ene-2-carboxylate 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以47%的产率得到(1R,2R,3R,4R,5R,7R)-7-benzyloxy-4,5-dihydroxy-5-methoxy-2-methoxycarbonyl-6-oxo-4,5-O-(diphenylmethylidene)bicyclo[2.2.2]octan-3-yl 2-acetamido-3,4,6-tri-O-acetyl-1,2-dideoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis, structural, and biological studies on a pseudodisaccharide containing a bicyclic, bridged carba-sugar

  摘要：

  Two carba-sugar containing pseudodisaccharide diastereomers have been synthesized from a racemic bicyclooctene derivative. The determination of the absolute configurations was carried out by means of CD measurements, CD calculations and X-ray diffraction. The compounds showed moderate competitive inhibitory effects on chondroitin AC-I lyase. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.07.023