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 | 130163-42-7

• 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)-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
• CAS: 130163-42-7
• 化学式: C₃₀H₅₃NO₁₆
• 分子量: 683.748
• InChiKey: PFQGXZAGDARCRZ-ASUIJKAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.44
• 重原子数：
  47.0
• 可旋转键数：
  17.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  252.39
• 氢给体数：
  8.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  GDP-L-colitose 、 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 以 水 为溶剂， 反应 30.0h， 以65%的产率得到9-[(2R,3R,4R,5S,6R)-3-Acetylamino-6-hydroxymethyl-4-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5-((2S,3S,4R,5R)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester
  参考文献：
  名称：

  Chemical synthesis of GDP-fucose analogs and their utilization by the Lewis *A(1 → 4) fucosyltransferase

  摘要：

  报道了GDP-岩藻糖（5）、GDP-3-去氧岩藻糖（6）和GDP-阿拉伯糖（7）的化学合成，其中7是5的去甲基类似物。当以*BDGal(1 → 3)*BDGlcNAc-O(CH₂)₈COOMe (1)作为受体时，发现这三种糖核苷酸都能作为人乳中分离的α(1 → 4)岩藻糖基转移酶的供体底物。使用耦合分光光度法测量糖残基转移速率，发现对1的转移率分别为100%（5）、2.3%（6）和5.9%（7）。通过酶联免疫吸附试验（ELISA）和¹H NMR光谱法鉴定了产物Le^a-活性寡糖类似物。关键词：糖基转移酶、寡糖合成、糖核苷酸类似物、ELISA检测、岩藻糖基转移酶。

  DOI：

  10.1139/v90-165
• 作为产物：
  描述：

  ethyl 2,4-di-O-benzyl-3,6-dideoxy-1-thio-β-L-xylo-hexopyranoside 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