9-[(2R,3R,4R,5S,6R)-4-((2R,3R,4S,5S,6R)-3-Acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-acetylamino-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester | 190248-90-9

• 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)-4-((2R,3R,4S,5S,6R)-3-Acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-acetylamino-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester
• CAS: 190248-90-9
• 化学式: C₅₄H₆₉NO₁₄
• 分子量: 956.14
• InChiKey: KIBOLGMBCBMQSA-VVIZNYEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.14
• 重原子数：
  69.0
• 可旋转键数：
  28.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  175.77
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  9-[(2R,3R,4R,5S,6R)-4-((2R,3R,4S,5S,6R)-3-Acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-acetylamino-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester 在 palladium on activated charcoal methanolate 、 2,4-di(tert-butyl)-4-methylpyridine 、 4 A molecular sieve 、 Amberlite OH^- 、 氢气 、 DMTST 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 0.27h， 生成 9-[(2R,3R,4R,5S,6R)-3-Acetylamino-5-((2S,3S,5S,6S)-3,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-6-hydroxymethyl-4-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester
  参考文献：
  名称：

  Synthesis of colitose-containing oligosaccharide structures found in polysaccharides from Vibrio cholerae O139 synonym Bengal using thioglycoside donors

  摘要：

  The syntheses of the two colitose-containing trisaccharides 8-methoxycarbonyloctyl (3,6-dideoxy-alpha-L-xylo-hexopyranosyl)-(1 --> 2)-beta-D-galactopyranosyl-(1 --> 3)-2-acetamido-2-deoxy-beta-D-glucopyranoside and 8-methoxycarbonyloctyl beta-D-galactopyranosyl-(1 --> 3)-[(3,6-dideoxy-alpha-L-xylo-hexopyranosyl)-(1 --> 4)]-2-acetamido-2-deoxy-beta-D-glueopyranoside, and tetrasaccharide 8-methoxycarbonyloctyl (3,6-dideoxy-alpha-L-xylo-hexopyranosyl)-(1 --> 2)-beta-D-galactopyranosyl-(1 --> 3)-[(3,6-dideoxy-alpha-L-xylo-hexopyranosyl)-(1 --> 4)]-2-acetamido-2-deoxy-beta-D-glucopyranoside are described. The oligosaccharides correspond to structures found in the capsular polysaccharide and the lipopolysaccharide of Vibrio cholerae O139 and also to lipopolysaccharide structures of E. coli O55 and Salmonella greenside. The colitose residues were introduced via dimethyl(methylthio)sulfonium trifluoromethanesulfonate promoted glycosylations using colitose thioglycosides as glycosyl donors. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00003-7
• 作为产物：
  描述：

  9-[(4aR,6R,7R,8R,8aS)-8-((2R,3R,4S,5S,6R)-3-Acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-7-acetylamino-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-nonanoic acid methyl ester 在 盐酸 、 sodium cyanoborohydride 作用下， 以 乙醚 为溶剂， 以77%的产率得到9-[(2R,3R,4R,5S,6R)-4-((2R,3R,4S,5S,6R)-3-Acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-acetylamino-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester
  参考文献：
  名称：

  Synthesis of colitose-containing oligosaccharide structures found in polysaccharides from Vibrio cholerae O139 synonym Bengal using thioglycoside donors

  摘要：

  The syntheses of the two colitose-containing trisaccharides 8-methoxycarbonyloctyl (3,6-dideoxy-alpha-L-xylo-hexopyranosyl)-(1 --> 2)-beta-D-galactopyranosyl-(1 --> 3)-2-acetamido-2-deoxy-beta-D-glucopyranoside and 8-methoxycarbonyloctyl beta-D-galactopyranosyl-(1 --> 3)-[(3,6-dideoxy-alpha-L-xylo-hexopyranosyl)-(1 --> 4)]-2-acetamido-2-deoxy-beta-D-glueopyranoside, and tetrasaccharide 8-methoxycarbonyloctyl (3,6-dideoxy-alpha-L-xylo-hexopyranosyl)-(1 --> 2)-beta-D-galactopyranosyl-(1 --> 3)-[(3,6-dideoxy-alpha-L-xylo-hexopyranosyl)-(1 --> 4)]-2-acetamido-2-deoxy-beta-D-glucopyranoside are described. The oligosaccharides correspond to structures found in the capsular polysaccharide and the lipopolysaccharide of Vibrio cholerae O139 and also to lipopolysaccharide structures of E. coli O55 and Salmonella greenside. The colitose residues were introduced via dimethyl(methylthio)sulfonium trifluoromethanesulfonate promoted glycosylations using colitose thioglycosides as glycosyl donors. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00003-7