methyl 6-O-(2-benzyloxycarbonylamino-2-deoxy-4-O-isobutyryl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside | 1194234-19-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-(2-benzyloxycarbonylamino-2-deoxy-4-O-isobutyryl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: CbzNH(-2d)[isobutyryl(-4)]Glc(b1-6)[Bn(-2)][Bn(-3)][Bn(-4)]a-Glc1Me；[(2R,3S,4R,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-5-(phenylmethoxycarbonylamino)oxan-3-yl] 2-methylpropanoate
• CAS: 1194234-19-9
• 化学式: C₄₆H₅₅NO₁₃
• 分子量: 829.942
• InChiKey: MDVCMIHQGZKZNW-FNTGYGFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  60
• 可旋转键数：
  21
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  170
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl-β(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 在 2,4,6-三甲基吡啶 、 (2S,5S)-2,5-bis[[(2S)-3-(1H-indol-3-yl)-1-(octyloxy)-1-oxopropan-2-ylamino]carbonyl]-1-(pyridin-4-yl)pyrrolidine 、 sodium methylate 、 potassium carbonate 、 一水合肼 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 22.0h， 生成 methyl 6-O-(2-benzyloxycarbonylamino-2-deoxy-4-O-isobutyryl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Functional Group Tolerance in Organocatalytic Regioselective Acylation of Carbohydrates

  摘要：

  Organocatalytic regioselective acylation of mono- and disaccaharides with various functionalized acid anhydrides has been developed. Acylation Of octyl beta-D-glucopyranoside with acid anhydrides derived from alpha-amino acids, cinnamic acid, and gallic acid took place at C(4)-OH with 67-94% regioselectivity in the presence of catalyst 1. Regioselective acylation of disaccharides with functionalized acid anhydrides was also achieved with 78-94% selectivity. Especially, a disaccharide with seven free hydroxy groups (X = OH, R' = H) underwent acylation at C(4)-OH with 78% regioselectivity in the presence of 1. Thus, functional group tolerance in the regioselective acylation catalyzed by I was found to be high.

  DOI：

  10.1021/jo901569v