benzyl 2,3,4-tri-O-benzyl-6-O-tertbutoxycarboxymethyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 431899-02-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,3,4-tri-O-benzyl-6-O-tertbutoxycarboxymethyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS: 431899-02-4
• 化学式: C₆₇H₇₄O₁₃
• 分子量: 1087.32
• InChiKey: PUIZNKXOJMULBC-WPIHNYCKSA-N

反应信息

• 作为反应物：
  描述：

  benzyl 2,3,4-tri-O-benzyl-6-O-tertbutoxycarboxymethyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 palladium dihydroxide 氢气 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 72.5h， 生成 6-O-carboxymethyl-β-D-galactopyranosyl-(1->4)-D-glucopyranose sodium salt
  参考文献：
  名称：

  Human milk oligosaccharides: an enzymatic protection step simplifies the synthesis of 3′- and 6′-O-sialyllactose and their analogues

  摘要：

  We describe a chemo-enzymatic synthesis of 3'- and 6'-O-sialyllactose, two trisaccharides occurring in the 'acidic fraction' of the human milk oligosaccharides and endowed with potential antiadhesive activity. The key step is the highly regioselective 6'-O-acylation of benzyllactoside, which gave access to suitably protected lactose building blocks to be used as acceptors in the sialylation reaction. Moreover, the synthesis of the carboxymethyl and sulfo analogues of the title compounds is reported. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00016-2
• 作为产物：
  描述：

  Dimethyl-(1,1,2-trimethyl-propyl)-[(2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethoxy]-silane 在 sodium hydroxide 、 四丁基氟化铵 、 水 、 四丁基硫酸氢铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 benzyl 2,3,4-tri-O-benzyl-6-O-tertbutoxycarboxymethyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Human milk oligosaccharides: an enzymatic protection step simplifies the synthesis of 3′- and 6′-O-sialyllactose and their analogues

  摘要：

  We describe a chemo-enzymatic synthesis of 3'- and 6'-O-sialyllactose, two trisaccharides occurring in the 'acidic fraction' of the human milk oligosaccharides and endowed with potential antiadhesive activity. The key step is the highly regioselective 6'-O-acylation of benzyllactoside, which gave access to suitably protected lactose building blocks to be used as acceptors in the sialylation reaction. Moreover, the synthesis of the carboxymethyl and sulfo analogues of the title compounds is reported. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00016-2