methyl 2,3,4,6-tetra-O-benzyl-1-C-methyl-α-D-glucopyranoside | 352020-91-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4,6-tetra-O-benzyl-1-C-methyl-α-D-glucopyranoside
• 英文别名: methyl 3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-hept-2-ulopyranoside；(2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-methoxy-2-methyltetrahydro-2H-pyran；(2S,3R,4S,5R,6R)-2-methoxy-2-methyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 352020-91-8
• 化学式: C₃₆H₄₀O₆
• 分子量: 568.71
• InChiKey: HWALAFXMYYPTOD-GJXDWMKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4,6-tetra-O-benzyl-1-C-methyl-α-D-glucopyranoside 在 palladium dihydroxide 吡啶 、 氢气 作用下， 以 甲醇 为溶剂， 生成 methyl 2,3,4,6-tetra-O-acetyl-1-C-methyl-α-D-glucopyranoside
  参考文献：
  名称：

  A facile synthesis of 1′-C-alkyl-α-disaccharides from 1-C-alkyl-hexopyranoses and methyl 1-C-methyl-hexopyranosides

  摘要：

  Direct O-glycosidations using the 1-C-alkyl-2,3,4,6-tetra-O-benzyl-hexopyranoses as the glycosyl donors were carried out with a catalytic amount (0.2 equiv.) of trimethylsilyl trifluoromethanesulfonate (TMSOTf). The glycosidations proceeded alpha -stereoselectively and furnished the corresponding 1'-C-alkyl-alpha -disaccharides in 71-90% yields. The O-transglycosidations from the benzylated and acetylated methyl I-C-methyl-or-hexopyranosides to the corresponding 1'-C-methyl-alpha -O-disaccharides were also examined, respectively. These transglycosidations took place on alpha -stereoselectivity and provided the 1'-C-methyl-alpha -O-disaccharides as the sole products, implying that no neighboring group participation occured in the reactions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00321-0
• 作为产物：
  描述：

  5-内酯 在 3 A molecular sieve 、 三氟化硼乙醚 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 7.08h， 生成 methyl 2,3,4,6-tetra-O-benzyl-1-C-methyl-α-D-glucopyranoside
  参考文献：
  名称：

  酮基吡喃糖基糖苷的合成及其基于三键碳-质子偶合的异头构型的确定。

  摘要：

  由相应的硫代糖苷合成了在Cα，Cβ和Cγ处具有多个取代基的酮基吡喃糖基糖苷对，并研究了Cα-Cβ-Cγ-的影响。研究了H（γ）扭转角和取代基对三键碳-质子耦合的影响。顺式耦合常数范围为1到2Hz。跨耦合通常小至2.3-2.6Hz；反之亦然。然而，对于带有未取代的γ-碳的化合物，测得的反式耦合相对较大（4.8Hz）。与相应的O-糖苷相比，β-位的S-乙基增加了顺式偶联（高达3.2Hz）。

  DOI：

  10.1016/j.carres.2007.05.006

文献信息

• A facile synthesis of 1′-C-alkyl-α-disaccharides from 1-C-alkyl-hexopyranoses and methyl 1-C-methyl-hexopyranosides
  作者：Xiaoliu Li、Hiro Ohtake、Hideyo Takahashi、Shiro Ikegami

  DOI：10.1016/s0040-4020(01)00321-0

  日期：2001.5

  Direct O-glycosidations using the 1-C-alkyl-2,3,4,6-tetra-O-benzyl-hexopyranoses as the glycosyl donors were carried out with a catalytic amount (0.2 equiv.) of trimethylsilyl trifluoromethanesulfonate (TMSOTf). The glycosidations proceeded alpha -stereoselectively and furnished the corresponding 1'-C-alkyl-alpha -disaccharides in 71-90% yields. The O-transglycosidations from the benzylated and acetylated methyl I-C-methyl-or-hexopyranosides to the corresponding 1'-C-methyl-alpha -O-disaccharides were also examined, respectively. These transglycosidations took place on alpha -stereoselectivity and provided the 1'-C-methyl-alpha -O-disaccharides as the sole products, implying that no neighboring group participation occured in the reactions. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of ketopyranosyl glycosides and determination of their anomeric configuration on the basis of the three-bond carbon–proton couplings
  作者：Gábor Májer、Anikó Borbás、Tünde Zita Illyés、László Szilágyi、Attila Csaba Bényei、András Lipták

  DOI：10.1016/j.carres.2007.05.006

  日期：2007.8

  Anomeric pairs of ketopyranosyl glycosides with various substituents at C(alpha), C(beta) and C(gamma) were synthesized from the corresponding thioglycosides, and the influence of the C(alpha)-C(beta)-C(gamma)-H(gamma) torsion angle and substituent effects on the three-bond carbon-proton couplings was studied. The cis coupling constants range from 1 to 2Hz. The trans couplings are generally as small

  由相应的硫代糖苷合成了在Cα，Cβ和Cγ处具有多个取代基的酮基吡喃糖基糖苷对，并研究了Cα-Cβ-Cγ-的影响。研究了H（γ）扭转角和取代基对三键碳-质子耦合的影响。顺式耦合常数范围为1到2Hz。跨耦合通常小至2.3-2.6Hz；反之亦然。然而，对于带有未取代的γ-碳的化合物，测得的反式耦合相对较大（4.8Hz）。与相应的O-糖苷相比，β-位的S-乙基增加了顺式偶联（高达3.2Hz）。