methyl 4,6-benzylidene-2-O-benzoyl-3-O-(3,4-di-O-(carbonyl)-2,6-dideoxy-2-bromo-β-D-galactopyranosyl)-(1->3)-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4,6-benzylidene-2-O-benzoyl-3-O-(3,4-di-O-(carbonyl)-2,6-dideoxy-2-bromo-β-D-galactopyranosyl)-(1->3)-α-D-glucopyranoside
• 英文别名: [(2R,4aR,6S,7R,8S,8aR)-8-[[(3aS,4R,6S,7R,7aS)-7-bromo-4-methyl-2-oxo-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] benzoate
• 化学式: C₂₈H₂₉BrO₁₁
• 分子量: 621.436
• InChiKey: BGWAPGKGLWJWID-JUPFSNASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  3,4-di-O-(carbonyl)-6-deoxy-D-galactal 在 N-溴代丁二酰亚胺(NBS) 、 叔丁基二甲硅基三氟甲磺酸酯 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.83h， 生成 methyl 4,6-benzylidene-2-O-benzoyl-3-O-(3,4-di-O-(carbonyl)-2,6-dideoxy-2-bromo-β-D-galactopyranosyl)-(1->3)-α-D-glucopyranoside
  参考文献：
  名称：

  Stereoselective Synthesis of 2-Deoxy-β-Galactosides via 2-Deoxy-2-bromo- and 2-Deoxy-2-iodo-galactopyranosyl Donors

  摘要：

  A series of 2-bromo- and 2-iodo-galactopyranosyl acetates and trichloroacetimidates were evaluated as glycosyl donors for the synthesis of 2-deoxygalactopyranosides. The best selectivity for the beta-glycosidic linkage was achieved by using 6-deoxy-3,4-carbonate-protected galactosyl donors.

  DOI：

  10.1021/ol034393t

文献信息

• Stereoselective Synthesis of 2-Deoxy-β-Galactosides via 2-Deoxy-2-bromo- and 2-Deoxy-2-iodo-galactopyranosyl Donors
  作者：Timothy B. Durham、William R. Roush

  DOI：10.1021/ol034393t

  日期：2003.5.1

  A series of 2-bromo- and 2-iodo-galactopyranosyl acetates and trichloroacetimidates were evaluated as glycosyl donors for the synthesis of 2-deoxygalactopyranosides. The best selectivity for the beta-glycosidic linkage was achieved by using 6-deoxy-3,4-carbonate-protected galactosyl donors.