benzyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-(2->3)-6-levulinoyl-β-D-galactopyranosyl-(1->4)-2,6-di-O-benzoyl-β-D-glucopyranoside | 431898-90-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-(2->3)-6-levulinoyl-β-D-galactopyranosyl-(1->4)-2,6-di-O-benzoyl-β-D-glucopyranoside
• 英文别名: methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4S,5R,6R)-5-benzoyloxy-2-(benzoyloxymethyl)-4-hydroxy-6-phenylmethoxyoxan-3-yl]oxy-3,5-dihydroxy-6-(4-oxopentanoyloxymethyl)oxan-4-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 431898-90-7
• 化学式: C₅₈H₆₉NO₂₇
• 分子量: 1212.18
• InChiKey: ZTFUTHFMWALXJI-RXJHYFJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  86
• 可旋转键数：
  34
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  373
• 氢给体数：
  4
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  benzyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-(2->3)-6-levulinoyl-β-D-galactopyranosyl-(1->4)-2,6-di-O-benzoyl-β-D-glucopyranoside 在 palladium on activated charcoal sodium methylate 、 sodium hydroxide 、 水 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 72.0h， 以84%的产率得到sialyl-α-(2->3')-lactose 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：

  benzyl 6-O-levulinoyl-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside 在 7 吡啶 、 苯甲酰腈 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 Sikkon 、 TEA 、 camphor-10-sulfonic acid 、 水 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 71.0h， 生成 benzyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-(2->3)-6-levulinoyl-β-D-galactopyranosyl-(1->4)-2,6-di-O-benzoyl-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

文献信息

• Human milk oligosaccharides: an enzymatic protection step simplifies the synthesis of 3′- and 6′-O-sialyllactose and their analogues
  作者：Anna Rencurosi、Laura Poletti、Marco Guerrini、Giovanni Russo、Luigi Lay

  DOI：10.1016/s0008-6215(02)00016-2

  日期：2002.3

  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.