1,6-anhydro-3-O-benzoyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-mannopyranose | 145742-75-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,6-anhydro-3-O-benzoyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-mannopyranose
• CAS: 145742-75-2
• 化学式: C₂₇H₃₂O₁₅
• 分子量: 596.542
• InChiKey: LSYAETYCGZCRTK-HLKLTAMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  42.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  188.65
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-3-O-benzoyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-mannopyranose 在 palladium on activated charcoal 吡啶 、 sodium azide 、 三氟甲磺酸三甲基硅酯 、 氢气 、 sodium methylate 、 乙酸肼 、 potassium carbonate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 152.5h， 生成 (1R,2R)-3-[(2R,3R,4R,5S,6R)-3-Amino-4-hydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-6-benzyloxy-cyclohexane-1,2,4,5-tetraol
  参考文献：
  名称：

  Building blocks for the synthesis of glycosyl-myo-inositols involved in the insulin intracellular signalling process

  摘要：

  Glycosylation of (+/-)-l-0-benzyl-2,3:5,6-di-0-isopropylidene-myo-inositol (4) with 6-O-acetyl-4-O-allyl-2-azido-3-0-benzyl-2-deoxy-beta-D-glucopyranosyl trichloroacetimidate (6) gave the 4-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-myo-inositol derivative (9) as a mixture of diastereoisomers which could be resolved by chromatography. Likewise alpha-glycosylation of 4 with 6-0-acetyl-2-azido-3-0-benzoyl-2-de-oxy-4-0-(2,3,4,6-tetra-0-acetyl-beta-D-galactopyranosyl)-D-glucopyranosyl trichloroacetimidate (10) gave the corresponding pseudotrisaccharide derivative 16 as a mixture of diastereomers which could be resolved partially by chromatography. alpha-Glycosylation of enantiomerically pure 2,3:5,6- (18) and 2,3:4,5-di-0-isopropylidene-1-0-menthoxycarbonyl-myo-inositol (19) with 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-glucopyranosyl trichloroacetimidate (20) gave the pseudodisaccharide derivatives 21 and 22, respectively. Likewise, alpha-glycosylation of 18 with 10 afforded a pseudotrisaccharide derivative (23).

  DOI：

  10.1016/0008-6215(92)85041-w
• 作为产物：
  描述：

  1,6-anhydro-2,3-O-benzylidene-β-D-mannopyranose 在 4 A molecular sieve 、 氰化汞 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 mercury dibromide 作用下， 以 二氯甲烷 、 水 、 苯 为溶剂， 反应 96.0h， 生成 1,6-anhydro-3-O-benzoyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-mannopyranose
  参考文献：
  名称：

  Building blocks for the synthesis of glycosyl-myo-inositols involved in the insulin intracellular signalling process

  摘要：

  Glycosylation of (+/-)-l-0-benzyl-2,3:5,6-di-0-isopropylidene-myo-inositol (4) with 6-O-acetyl-4-O-allyl-2-azido-3-0-benzyl-2-deoxy-beta-D-glucopyranosyl trichloroacetimidate (6) gave the 4-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-myo-inositol derivative (9) as a mixture of diastereoisomers which could be resolved by chromatography. Likewise alpha-glycosylation of 4 with 6-0-acetyl-2-azido-3-0-benzoyl-2-de-oxy-4-0-(2,3,4,6-tetra-0-acetyl-beta-D-galactopyranosyl)-D-glucopyranosyl trichloroacetimidate (10) gave the corresponding pseudotrisaccharide derivative 16 as a mixture of diastereomers which could be resolved partially by chromatography. alpha-Glycosylation of enantiomerically pure 2,3:5,6- (18) and 2,3:4,5-di-0-isopropylidene-1-0-menthoxycarbonyl-myo-inositol (19) with 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-glucopyranosyl trichloroacetimidate (20) gave the pseudodisaccharide derivatives 21 and 22, respectively. Likewise, alpha-glycosylation of 18 with 10 afforded a pseudotrisaccharide derivative (23).

  DOI：

  10.1016/0008-6215(92)85041-w