3-nitropyridyl-2-(benzyl 2,3,4-tri-O-benzyl-α-D-galactopyranosid)thiouronate | 141118-06-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-nitropyridyl-2-(benzyl 2,3,4-tri-O-benzyl-α-D-galactopyranosid)thiouronate
• 英文别名: S-(3-nitropyridin-2-yl) (2S,3R,4S,5R,6S)-3,4,5,6-tetrakis(phenylmethoxy)oxane-2-carbothioate
• CAS: 141118-06-1
• 化学式: C₃₉H₃₆N₂O₈S
• 分子量: 692.789
• InChiKey: SQRNMSUKGMZLFI-SZSPXRLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.31
• 重原子数：
  50.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  119.25
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3-nitropyridyl-2-(benzyl 2,3,4-tri-O-benzyl-α-D-galactopyranosid)thiouronate 在 正丁基锂 、 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， 反应 48.75h， 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：

  phenylmethyl (phenylmethyl α-D-galactopyranosid)uronate 在 lithium hydroxide 、 甲基三辛基氯化铵 、 三苯基膦 、 silver(l) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 28.0h， 生成 3-nitropyridyl-2-(benzyl 2,3,4-tri-O-benzyl-α-D-galactopyranosid)thiouronate
  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