2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl (benzyl 2,3,4-tri-O-benzyl-α-D-galactopyranosid)uronate | 141118-08-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl (benzyl 2,3,4-tri-O-benzyl-α-D-galactopyranosid)uronate
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] (2S,3R,4S,5R,6S)-3,4,5,6-tetrakis(phenylmethoxy)oxane-2-carboxylate
• CAS: 141118-08-3
• 化学式: C₆₈H₆₈O₁₂
• 分子量: 1077.28
• InChiKey: ORVMZLOYPIFYNY-PCRCZGOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.93
• 重原子数：
  80.0
• 可旋转键数：
  27.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  118.6
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl (benzyl 2,3,4-tri-O-benzyl-α-D-galactopyranosid)uronate 在 W-2 Raney nickel 、 2,4-双(4-苯氧苯基)-1,3-二硫杂-2,4-二磷杂环丁烷-2,4-二硫化物 作用下， 生成 benzyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-D-galactopyranoside
  参考文献：
  名称：

  Redox glycosidation: stereoselective syntheses of (1.fwdarw.6) linked disaccharides via thionoester intermediates

  摘要：

  Perbenzyl derivatives of the disaccharides benzyl 6-O-(alpha(and beta)-D-glucopyranosyl)-alpha-D-galactopyranoside and benzyl 6-O-(alpha(and beta)-D-mannopyranosyl)-alpha-D-galactopyranoside were each prepared in a stereoselective manner by acylation, thionation, and reductive desulfurization. The use of 2,4-bis(4-phenoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (4b) as a mild thionation reagent for esters and lactones is also described.

  DOI：

  10.1021/jo00036a012
• 作为产物：
  描述：

  benzyl (benzyl 2,3,4-tri-O-benzyl-α-D-galactopyranosid)uronate 在 lithium hydroxide 、 正丁基锂 、 甲基三辛基氯化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 4.75h， 生成 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl (benzyl 2,3,4-tri-O-benzyl-α-D-galactopyranosid)uronate
  参考文献：
  名称：

  Redox glycosidation: stereoselective syntheses of (1.fwdarw.6) linked disaccharides via thionoester intermediates

  摘要：

  Perbenzyl derivatives of the disaccharides benzyl 6-O-(alpha(and beta)-D-glucopyranosyl)-alpha-D-galactopyranoside and benzyl 6-O-(alpha(and beta)-D-mannopyranosyl)-alpha-D-galactopyranoside were each prepared in a stereoselective manner by acylation, thionation, and reductive desulfurization. The use of 2,4-bis(4-phenoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (4b) as a mild thionation reagent for esters and lactones is also described.

  DOI：

  10.1021/jo00036a012