methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside | 1330629-51-0

• 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-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside
• 英文别名: Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Glc(a1-6)[Bn(-2)][Bn(-3)][Bn(-4)]Glc(a1-6)[Bz(-2)][Bz(-3)][Bz(-4)]a-Glc1Me；[(2R,3R,4S,5R,6S)-4,5-dibenzoyloxy-6-methoxy-2-[[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-[[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]oxan-3-yl] benzoate
• CAS: 1330629-51-0
• 化学式: C₈₉H₈₈O₁₉
• 分子量: 1461.67
• InChiKey: LGCDWXFUCUAXRO-HWUDNGSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14
• 重原子数：
  108
• 可旋转键数：
  38
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  199
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  甲基2,3,4-三-O-苯甲酰-α-D-吡喃葡萄糖苷 、 2,3,4,6-四苄基-D-吡喃葡萄糖 、 2,3,4-tri-O-benzyl-D-glucopyranosyl trichloroacetate 在 三氯乙酰异氰酸酯 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 乙醚 为溶剂， 反应 5.0h， 生成 methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside 、 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside 、 methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside 、 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  Sequential one-pot glycosylation with glycosyl N-trichloroacetylcarbamate and trichloroacetate including dehydrative approach using 1-hydroxy sugars

  摘要：

  An efficient sequential one-pot glycosylation has been developed with glycosyl trichlorocarbamate and trichloroacetate activated by the same Lewis acid and enabled by a change in reaction temperature. The act-selective glycosylation was achieved using glucose, galactose, and mannose substrates after investigation into the reactivities of the two types of glycosyl donors. Sequential one-pot dehydrative glycosylation, including in situ preparation of glycosyl donors followed by generation of two glycosyl bonds, provided three types of trisaccharide. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2011.06.006

文献信息

• Sequential one-pot glycosylation with glycosyl N-trichloroacetylcarbamate and trichloroacetate including dehydrative approach using 1-hydroxy sugars
  作者：Tatsuya Shirahata、Asami Kojima、Satoko Teruya、Jun-ichi Matsuo、Masaki Yokoyama、Shogo Unagiike、Toshiaki Sunazuka、Kazuishi Makino、Eisuke Kaji、Satoshi Ōmura、Yoshinori Kobayashi

  DOI：10.1016/j.tet.2011.06.006

  日期：2011.9

  An efficient sequential one-pot glycosylation has been developed with glycosyl trichlorocarbamate and trichloroacetate activated by the same Lewis acid and enabled by a change in reaction temperature. The act-selective glycosylation was achieved using glucose, galactose, and mannose substrates after investigation into the reactivities of the two types of glycosyl donors. Sequential one-pot dehydrative glycosylation, including in situ preparation of glycosyl donors followed by generation of two glycosyl bonds, provided three types of trisaccharide. (C) 2011 Published by Elsevier Ltd.