methyl 2,6-dibenzyl-3-methyl-α-D-mannopyranosyl-(1->4)-2,6-dibenzyl-3-methyl-α-D-mannopyranoside | 187732-24-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,6-dibenzyl-3-methyl-α-D-mannopyranosyl-(1->4)-2,6-dibenzyl-3-methyl-α-D-mannopyranoside
• 英文别名: Bn(-2)[Bn(-6)]Man3Me(a1-4)[Bn(-2)][Bn(-6)]a-Man1Me3Me；(2R,3R,4S,5S,6R)-6-[(2R,3R,4S,5S,6S)-4,6-dimethoxy-5-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-4-methoxy-5-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-ol
• CAS: 187732-24-7
• 化学式: C₄₃H₅₂O₁₁
• 分子量: 744.879
• InChiKey: XILQCWFQQVHDOC-ZGCOVRMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  54
• 可旋转键数：
  19
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 2,6-dibenzyl-3-methyl-α-D-mannopyranosyl-(1->4)-2,6-dibenzyl-3-methyl-α-D-mannopyranoside 在 palladium on activated charcoal 吡啶 、 三氟甲磺酸三甲基硅酯 、 氢气 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 8.5h， 生成 methyl α-D-mannopyranosyl-(1->4)-3-methyl-α-D-mannopyranosyl-(1->4)-3-methyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of MethylO-α-D-Mannosyl-(1→4)-[(3-O-methyl-α-D- mannosyl)-(1→4)-]_n3-O-methyl-α-D-mannosides (n= 0, 1, and 2) via Dehydrative Glycosylation

  摘要：

  通过脱水糖基化反应合成了甲基 O-α-D-吡喃甘露糖基-(1→4)-[(3-O-甲基-α-D-吡喃甘露糖基-(1→4)-]n3-O-甲基-α-D-吡喃甘露糖苷（n = 0、1 和 2），这是分枝杆菌中 3-O-甲基甘露糖多糖（MMP）的最低同源物。由对硝基苯磺酰氯、三氟甲磺酸银和三乙胺，对硝基苯磺酰氯、三氟甲磺酸银和 1，8-二氮杂双环[5.4.0]十一-7-烯，以及三氟甲磺酸三甲基硅酯和吡啶组成的试剂体系非常有用。

  DOI：

  10.1246/bcsj.75.1301
• 作为产物：
  描述：

  allyl 2,6-dibenzyl-3-methyl-α-D-mannopyranoside 在 palladium dichloride 吡啶 、 sodium methylate 、 sodium acetate 、 silver trifluoromethanesulfonate 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 对硝基苯磺酰氯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 methyl 2,6-dibenzyl-3-methyl-α-D-mannopyranosyl-(1->4)-2,6-dibenzyl-3-methyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of MethylO-α-D-Mannosyl-(1→4)-[(3-O-methyl-α-D- mannosyl)-(1→4)-]_n3-O-methyl-α-D-mannosides (n= 0, 1, and 2) via Dehydrative Glycosylation

  摘要：

  通过脱水糖基化反应合成了甲基 O-α-D-吡喃甘露糖基-(1→4)-[(3-O-甲基-α-D-吡喃甘露糖基-(1→4)-]n3-O-甲基-α-D-吡喃甘露糖苷（n = 0、1 和 2），这是分枝杆菌中 3-O-甲基甘露糖多糖（MMP）的最低同源物。由对硝基苯磺酰氯、三氟甲磺酸银和三乙胺，对硝基苯磺酰氯、三氟甲磺酸银和 1，8-二氮杂双环[5.4.0]十一-7-烯，以及三氟甲磺酸三甲基硅酯和吡啶组成的试剂体系非常有用。

  DOI：

  10.1246/bcsj.75.1301

文献信息

• Synthesis of a hexasaccharide acceptor corresponding to the reducing terminus of mycobacterial 3-O-methylmannose polysaccharide (MMP)
  作者：Wensheng Liao、Depei Lu

  DOI：10.1016/s0008-6215(96)00239-x

  日期：1996.12

  The title compound methyl O-(2,6-di-O-benzyl-3-O-methyl-alpha-D-mannopyranosyl)-[(1 --> 4)- O-(2,6-di-O-benzyl-3-O-methyl-alpha-D-mannopyranosyl)](4)-(1 --> 4)-2,6-di-O-benzyl-3-O-methyl-alpha-D- mannopyranoside (2) was synthesized in a blockwise manner, employing trichloroacetimidate (11) and (20) as glycosyl donors. The strategy relies on the single-step preparation of the 3-O-methyl ethers (4) and (12) as starting materials. Since all intermediates contain one or more OCH3 groups, they are easily identified by NMR spectroscopy using the methyl proton signals, Compound 2 corresponds to the reducing terminal hexasaccharide of mycobacterial 3-O-methylmannose polysaccharide (MMP). MMP has the unusual property of stimulating the fatty acid synthetase multienzyme complex. Compound 2 can serve as a suitable glycosyl acceptor for the synthesis of extended fragments of MMP. (C) 1996 Elsevier Science-Ltd.
• Synthesis of Methyl<i>O</i>-<i>α</i>-D-Mannosyl-(1→4)-[(3-<i>O</i>-methyl-<i>α</i>-D- mannosyl)-(1→4)-]_<i>n</i>3-<i>O</i>-methyl-<i>α</i>-D-mannosides (<i>n</i>= 0, 1, and 2) via Dehydrative Glycosylation
  作者：Motoko Hirooka、Megumi Terayama、Emi Mitani、Shinkiti Koto、Asako Miura、Kayo Chiba、Ayano Takabatake、Takako Tashiro

  DOI：10.1246/bcsj.75.1301

  日期：2002.6

  Methyl O-α-D-mannopyranosyl-(1→4)-[(3-O-methyl-α-D-mannopyranosyl-(1→4)-]n3-O-methyl-α-D-mannopyranosides (n = 0, 1, and 2), the lowest homologs related to the 3-O-methylmannose polysaccharides (MMP) from Mycobacterium smegmatis, were synthesized via dehydrative glycosylation reactions. The reagent systems, composed of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine, of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and 1, 8-diazabicyclo[5.4.0]undec-7-ene, and of trimethylsilyl trifuloromethanesulfonate and pyridine were useful.

  通过脱水糖基化反应合成了甲基 O-α-D-吡喃甘露糖基-(1→4)-[(3-O-甲基-α-D-吡喃甘露糖基-(1→4)-]n3-O-甲基-α-D-吡喃甘露糖苷（n = 0、1 和 2），这是分枝杆菌中 3-O-甲基甘露糖多糖（MMP）的最低同源物。由对硝基苯磺酰氯、三氟甲磺酸银和三乙胺，对硝基苯磺酰氯、三氟甲磺酸银和 1，8-二氮杂双环[5.4.0]十一-7-烯，以及三氟甲磺酸三甲基硅酯和吡啶组成的试剂体系非常有用。