methyl 2,3,6-tri-O-acetyl-4-O-(2,6-di-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside | 132410-52-7

• 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 2,3,6-tri-O-acetyl-4-O-(2,6-di-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-5-acetyloxy-6-[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-methylsulfanyloxan-3-yl]oxy-3,4-dihydroxyoxan-2-yl]methyl acetate
• CAS: 132410-52-7
• 化学式: C₂₃H₃₄O₁₅S
• 分子量: 582.58
• InChiKey: KXXUEJPXTHLORG-CSKYTZDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  225
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  methyl 2,3,6-tri-O-acetyl-4-O-(2,6-di-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 四丁基碘化铵 、 二正丁基氧化锡 、 nitrosonium tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 52.5h， 生成 methyl 2-acetamido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-6-O-<2,3,6-tri-O-acetyl-4-O-(2,4,6-tri-O-acetyl-3-O-methyl-β-D-galactopyranosyl)-β-D-glucopyranosyl>-3-O-benzyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthetic oligosaccharides related to group B streptococcal polysaccharides. 5. Combined chemical and enzymic synthesis of a pentasaccharide repeating unit of the capsular polysaccharide of type III group B Streptococcus and one- and two-dimensional NMR spectroscopic studies

  摘要：

  A combination of chemical and enzymatic methods is described for the synthesis of the branching pentasaccharide 3-OMe-beta-D-Galp-(1 --> 4)-beta-D-Glcp-(1 --> 6)-[alpha-D-Neup5Ac-(2 --> 3)-beta-D-Galp-(1 --> 4)]-beta-D-GlcpNAc-OMe (4). Pentasaccharide 4, represents a complete repeating unit of the capsular polysaccharide of type III group B Streptococci, which will be used as a molecular probe in the study of the fine specificities of carbohydrate-protein interactions. Key intermediate was the alcohol methyl 2-acetamido-3-O-benzyl-2-deoxy-6-O-(4-methoxy-benzyl)-beta-D-glucopyranoside (9), which was beta-D-galactosylated and chemoselectively deprotected to provide the beta-D-Galp-beta-D-GlcpNAc acceptor block 13. Two approaches are described for the synthesis of the beta-D-Galp-(1 --> 4)-beta-D-Glcp donor block 17, which was coupled to acceptor 13 under the agency of trimethylsilyl trifluoromethanesulfonate. Removal of the blocking groups from the fully protected tetrasaccharide 24 by transesterification and hydrogenolysis provided tetrasaccharide 5, which was sialylated enzymatically using a specific rat liver sialyltransferase to provide pentasaccharide 4. Complete assignment of the H-1 and C-13 NMR spectra of the tetra-5 and pentasaccharide 4 is presented, and their carbon spin-lattice relaxation times (T1) are also reported.

  DOI：

  10.1021/jo00010a037
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-acetyl-4-O-(2,6-di-O-acetyl-3,4-O-isopropylidene-β-d-galactopyranosyl)-1-thio-β-D-glucopyranoside 在 tetrafluoroboric acid 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以96.1%的产率得到methyl 2,3,6-tri-O-acetyl-4-O-(2,6-di-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthetic oligosaccharides related to group B streptococcal polysaccharides. 5. Combined chemical and enzymic synthesis of a pentasaccharide repeating unit of the capsular polysaccharide of type III group B Streptococcus and one- and two-dimensional NMR spectroscopic studies

  摘要：

  A combination of chemical and enzymatic methods is described for the synthesis of the branching pentasaccharide 3-OMe-beta-D-Galp-(1 --> 4)-beta-D-Glcp-(1 --> 6)-[alpha-D-Neup5Ac-(2 --> 3)-beta-D-Galp-(1 --> 4)]-beta-D-GlcpNAc-OMe (4). Pentasaccharide 4, represents a complete repeating unit of the capsular polysaccharide of type III group B Streptococci, which will be used as a molecular probe in the study of the fine specificities of carbohydrate-protein interactions. Key intermediate was the alcohol methyl 2-acetamido-3-O-benzyl-2-deoxy-6-O-(4-methoxy-benzyl)-beta-D-glucopyranoside (9), which was beta-D-galactosylated and chemoselectively deprotected to provide the beta-D-Galp-beta-D-GlcpNAc acceptor block 13. Two approaches are described for the synthesis of the beta-D-Galp-(1 --> 4)-beta-D-Glcp donor block 17, which was coupled to acceptor 13 under the agency of trimethylsilyl trifluoromethanesulfonate. Removal of the blocking groups from the fully protected tetrasaccharide 24 by transesterification and hydrogenolysis provided tetrasaccharide 5, which was sialylated enzymatically using a specific rat liver sialyltransferase to provide pentasaccharide 4. Complete assignment of the H-1 and C-13 NMR spectra of the tetra-5 and pentasaccharide 4 is presented, and their carbon spin-lattice relaxation times (T1) are also reported.

  DOI：

  10.1021/jo00010a037

文献信息

• POZSGAY, VINCE;BRISSON, JEAN-ROBERT;JENNINGS, HAROLD J.;ALLEN, STEVE;PAUL+, J. ORG. CHEM., 56,(1991) N0, C. 3377-3385
  作者：POZSGAY, VINCE、BRISSON, JEAN-ROBERT、JENNINGS, HAROLD J.、ALLEN, STEVE、PAUL+

  DOI：——

  日期：——