(2'S,3'S,4'R)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-2'-O-(para-methoxybenzyl)-D-ribo-heptadec-5',6'-enyl)-acetylene | 1221720-07-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2'S,3'S,4'R)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-2'-O-(para-methoxybenzyl)-D-ribo-heptadec-5',6'-enyl)-acetylene
• CAS: 1221720-07-5
• 化学式: C₆₄H₈₀O₉
• 分子量: 993.334
• InChiKey: KMIGVLQVWALOJP-UWDTYTRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.71
• 重原子数：
  73.0
• 可旋转键数：
  30.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  83.07
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2'S,3'S,4'R)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-2'-O-(para-methoxybenzyl)-D-ribo-heptadec-5',6'-enyl)-acetylene 在 4-二甲氨基吡啶 、 蜡酸 、 sodium acetate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 对甲苯磺酰肼 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 18.67h， 生成 (2'S,3'R,4'R)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-2'-O-hexacosanoyl-D-ribo-heptadecyl)-ethane
  参考文献：
  名称：

  Use of the NEO strategy (Nucleophilic addition/Epoxide Opening) for the synthesis of a new C-galactoside ester analogue of KRN 7000

  摘要：

  Our goal in the search for potentially bioactive analogues of KRN 7000 was to design an easy synthetic approach to a library of analogues using a strategy recently developed in our laboratory based on a Nucleophilic addition followed by an Epoxide Opening (the NEO strategy). Through the use of a common pivotal structure, a new C-galactoside ester analogue (23) was synthesized which showed an encouraging T(H)2 biased response during preliminary biological tests. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.044
• 作为产物：
  描述：

  2,3-O-isopropylidene-1-trimethylsilylacetylene-D-ribo-butan-1,4-diol 在 咪唑 、 4-二甲氨基吡啶 、 氟化铵 、 正丁基锂 、 草酰氯 、 四丁基碘化铵 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 (2'S,3'S,4'R)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-2'-O-(para-methoxybenzyl)-D-ribo-heptadec-5',6'-enyl)-acetylene
  参考文献：
  名称：

  Use of the NEO strategy (Nucleophilic addition/Epoxide Opening) for the synthesis of a new C-galactoside ester analogue of KRN 7000

  摘要：

  Our goal in the search for potentially bioactive analogues of KRN 7000 was to design an easy synthetic approach to a library of analogues using a strategy recently developed in our laboratory based on a Nucleophilic addition followed by an Epoxide Opening (the NEO strategy). Through the use of a common pivotal structure, a new C-galactoside ester analogue (23) was synthesized which showed an encouraging T(H)2 biased response during preliminary biological tests. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.044