9-[(2R,3R,4R,5S,6R)-5-Acetoxy-6-acetoxymethyl-3-allyloxycarbonylamino-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester | 194603-67-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-[(2R,3R,4R,5S,6R)-5-Acetoxy-6-acetoxymethyl-3-allyloxycarbonylamino-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester
• CAS: 194603-67-3
• 化学式: C₃₈H₅₇NO₂₀
• 分子量: 847.865
• InChiKey: GXGQDRFXQIRBOG-WYYTWPBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  59.0
• 可旋转键数：
  23.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  259.35
• 氢给体数：
  1.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  9-[(2R,3R,4R,5S,6R)-5-Acetoxy-6-acetoxymethyl-3-allyloxycarbonylamino-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester 在 甲醇 、 四(三苯基膦)钯 、 sodium methylate 、 sodium cacodylate 、 O-Benzotriazol-1-yl-N,N,N',N'-bis(tetramethylene)uronium hexafluorophosphate 、 三乙胺 、 丙二酸二乙酯 、 manganese(ll) chloride 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 8-methoxycarbonyloctyl 5-N-acetyl-α-neuraminyl-(2->3)-β-D-galactopyranosyl-(1->3)-2-deoxy-2-(methyl β-L-galactopyranosyluronamide)-β-D-glucopyranoside
  参考文献：
  名称：

  Glycosyltransferase catalyzed assemblage of sialyl-Lewisa-saccharopeptides

  摘要：

  A series of methyl hexopyranosiduronic acids are coupled to type I disaccharide amines to give 'trisaccharides' which have the natural N-acetyl group of the type I disaccharides replaced by uronic acids (--> saccharopeptides). These saccharopeptides are surprisingly good substrates for alpha-2,3-sialyltransferase and fucosyltransferase III. The enzymes transfer N-acetylneuraminic acid and fucose, respectively, onto these acceptor substrates, despite the far reaching alterations, regio- and stereospecifically in the expected manner to yield sialyl-Lewis(a)-saccharopeptides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00229-8
• 作为产物：
  描述：

  9-((2R,4aR,6R,7R,8R,8aS)-7-Allyloxycarbonylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-nonanoic acid methyl ester 在 吡啶 、 氰化汞 、 三氟乙酸 作用下， 以 硝基甲烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 生成 9-[(2R,3R,4R,5S,6R)-5-Acetoxy-6-acetoxymethyl-3-allyloxycarbonylamino-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester
  参考文献：
  名称：

  Glycosyltransferase catalyzed assemblage of sialyl-Lewisa-saccharopeptides

  摘要：

  A series of methyl hexopyranosiduronic acids are coupled to type I disaccharide amines to give 'trisaccharides' which have the natural N-acetyl group of the type I disaccharides replaced by uronic acids (--> saccharopeptides). These saccharopeptides are surprisingly good substrates for alpha-2,3-sialyltransferase and fucosyltransferase III. The enzymes transfer N-acetylneuraminic acid and fucose, respectively, onto these acceptor substrates, despite the far reaching alterations, regio- and stereospecifically in the expected manner to yield sialyl-Lewis(a)-saccharopeptides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00229-8

文献信息

• Enzymatic α(2–3)sialylation of non-natural type-I (Lewisc) disaccharides with recombinant sialyl-transferase
  作者：Gabi Baisch、Reinhold Öhrlein、Markus Streiff

  DOI：10.1016/s0960-894x(97)10201-3

  日期：1998.1

  Recombinant alpha(2-3)sialyl-transferase from rat liver is used to sialylate a series of type-I (Lewis(c)) disaccharides on a preparative scale. The enzyme tolerates a broad array of N-acetyl replacements of the N-glucosamine subunit ranging from small and large lipophilic groups to charged and heterocyclic amides. (C) 1998 Elsevier Science Ltd. All rights reserved.