(1R,2S,3S,4S,5R,6S,7S)-7-benzyloxy-4,5,6-trihydroxy-5-methoxy-2-methoxycarbonyl-4,5-O-(diphenylmethylidene)bicyclo[2.2.2]octan-3-yl 2-acetamido-1,2-dideoxy-1-thio-β-D-glucopyranoside | 1338920-59-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2S,3S,4S,5R,6S,7S)-7-benzyloxy-4,5,6-trihydroxy-5-methoxy-2-methoxycarbonyl-4,5-O-(diphenylmethylidene)bicyclo[2.2.2]octan-3-yl 2-acetamido-1,2-dideoxy-1-thio-β-D-glucopyranoside
• CAS: 1338920-59-4
• 化学式: C₃₉H₄₅NO₁₂S
• 分子量: 751.852
• InChiKey: MZGQLWYPXRNAPV-CXGXUJISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  53.0
• 可旋转键数：
  11.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  182.47
• 氢给体数：
  5.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (1R,2S,3S,4S,5R,6S,7S)-7-benzyloxy-4,5,6-trihydroxy-5-methoxy-2-methoxycarbonyl-4,5-O-(diphenylmethylidene)bicyclo[2.2.2]octan-3-yl 2-acetamido-1,2-dideoxy-1-thio-β-D-glucopyranoside 在 sodium tetrahydroborate 、 palladium 10% on activated carbon 、 氢气 、 三氟乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 27.0h， 生成 (1S,2R,3S,4S,5S,6S,7S)-4,5,6,7-tetrahydroxy-2-carboxybicyclo[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：

  (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 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 5.33h， 生成 (1R,2S,3S,4S,5R,6S,7S)-7-benzyloxy-4,5,6-trihydroxy-5-methoxy-2-methoxycarbonyl-4,5-O-(diphenylmethylidene)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