Acetic acid (2R,3R,4S,5S,6R)-5-benzyloxy-2-benzyloxymethyl-4-methoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester | 187732-11-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3R,4S,5S,6R)-5-benzyloxy-2-benzyloxymethyl-4-methoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester
• 英文别名: Bn(-2)[Bn(-6)]Man3Me4Ac(a)-O-C(NH)CCl3；[(2R,3R,4S,5S,6R)-4-methoxy-5-phenylmethoxy-2-(phenylmethoxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] acetate
• CAS: 187732-11-2
• 化学式: C₂₅H₂₈Cl₃NO₇
• 分子量: 560.859
• InChiKey: OZVRHOIWWXOBTF-MHMIHQHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  96.3
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5S,6R)-5-benzyloxy-2-benzyloxymethyl-4-methoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester 在 三乙基硅基三氟甲磺酸酯 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 4.25h， 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 a hexasaccharide acceptor corresponding to the reducing terminus of mycobacterial 3-O-methylmannose polysaccharide (MMP)

  摘要：

  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.

  DOI：

  10.1016/s0008-6215(96)00239-x
• 作为产物：
  描述：

  三氯乙腈 、 4-acetyl-2,6-dibenzyl-3-methyl-D-mannopyranose 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以92%的产率得到Acetic acid (2R,3R,4S,5S,6R)-5-benzyloxy-2-benzyloxymethyl-4-methoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis of a hexasaccharide acceptor corresponding to the reducing terminus of mycobacterial 3-O-methylmannose polysaccharide (MMP)

  摘要：

  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.

  DOI：

  10.1016/s0008-6215(96)00239-x