methyl 5-(2-acetoxy)acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate-(2->3)-4,6-di-O-benzyl-D-galactal | 1167992-10-0

• 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: methyl 5-(2-acetoxy)acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate-(2->3)-4,6-di-O-benzyl-D-galactal
• 英文别名: methyl (2R,4S,5R,6R)-4-acetyloxy-5-[(2-acetyloxyacetyl)amino]-2-[[(2R,3R,4R)-3-phenylmethoxy-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-4-yl]oxy]-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 1167992-10-0
• 化学式: C₄₂H₅₁NO₁₈
• 分子量: 857.863
• InChiKey: SWGIEEGAPJHDNQ-SYXNLRDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  61
• 可旋转键数：
  26
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  233
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  methyl (5-(2-acetoxy)acetamido-4,7,8,9-tetra-O-acetyl-2-dibenzylphosphityl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosid)onate 、 4,6-di-O-benzyl-D-galactal 在 三氟甲磺酸三甲基硅酯 作用下， 以 EtCN 为溶剂， 反应 0.17h， 以61%的产率得到methyl 5-(2-acetoxy)acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate-(2->3)-4,6-di-O-benzyl-D-galactal
  参考文献：
  名称：

  Sialylation using N-glycolylneuraminyl phosphite donors to synthesize Neu5Gc-containing glycans

  摘要：

  Efficient sialylations using N-glycolylneuraminic acid (Neu5Gc) phosphite donors having an acetyl or benzyl group on the glycolyl moiety are described in the synthesis of Neu5Gc-containing glycans. Both phosphite donors 1 and 2 were readily coupled with primary and secondary acceptor alcohols in propionitrile at -78 degrees C to provide the desired glycosides with good alpha-selectivities. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.03.004