2-O-benzyl-3,4-O-isopropylidene-α-L-fucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-galactopyranosyl trichloroacetimidate | 1610609-80-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-benzyl-3,4-O-isopropylidene-α-L-fucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-galactopyranosyl trichloroacetimidate
• CAS: 1610609-80-7
• 化学式: C₄₅H₅₀Cl₃NO₁₀
• 分子量: 871.252
• InChiKey: JZLGVWNKKCFGMS-GZFKKNKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  59.0
• 可旋转键数：
  16.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  116.15
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2-O-benzyl-3,4-O-isopropylidene-α-L-fucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-galactopyranosyl trichloroacetimidate 、 phenyl 2,3,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以84%的产率得到phenyl 2-O-benzyl-3,4-O-isopropylidene-α-L-fucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-galactopyranosyl-(1→4)-2,3,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Calocybe indica var. APK2 polysaccharide repeating unit

  摘要：

  The first total synthesis of p-methoxyphenyl alpha-L-fucopyranosyl-(1 -> 6)-alpha-D-galactopyranosyl-(1 -> 4)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranoside (2) was achieved starting from five monosaccharide building blocks. This structure represents the repeating unit of the polysaccharide isolated from edible mushroom Calocybe indica var. APK2, and was synthesized in high overall yield via a convergent '3+ 2' glycosylation strategy. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.04.004
• 作为产物：
  描述：

  ethyl 2-O-benzyl-3,4-O-isopropylidene-1-thio-β-L-fucopyranoside 在 N-碘代丁二酰亚胺 、 ammonium cerium (IV) nitrate 、 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 生成 2-O-benzyl-3,4-O-isopropylidene-α-L-fucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-galactopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of Calocybe indica var. APK2 polysaccharide repeating unit

  摘要：

  The first total synthesis of p-methoxyphenyl alpha-L-fucopyranosyl-(1 -> 6)-alpha-D-galactopyranosyl-(1 -> 4)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranoside (2) was achieved starting from five monosaccharide building blocks. This structure represents the repeating unit of the polysaccharide isolated from edible mushroom Calocybe indica var. APK2, and was synthesized in high overall yield via a convergent '3+ 2' glycosylation strategy. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.04.004