benzyl 2,3,4-tri-O-benzyl-α-D-galactopyranosiduronic acid | 141118-05-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,3,4-tri-O-benzyl-α-D-galactopyranosiduronic acid
• 英文别名: (2S,3R,4S,5R,6S)-3,4,5,6-tetrakis(phenylmethoxy)oxane-2-carboxylic acid
• CAS: 141118-05-0
• 化学式: C₃₄H₃₄O₇
• 分子量: 554.64
• InChiKey: DZTFRMXHQHBJOQ-XXFURDKYSA-N

物化性质

• 沸点：
  697.2±55.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.77
• 重原子数：
  41.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  benzyl 2,3,4-tri-O-benzyl-α-D-galactopyranosiduronic acid 在 正丁基锂 、 4-吡咯烷基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 36.5h， 生成 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl (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
• 作为产物：
  描述：

  phenylmethyl (phenylmethyl α-D-galactopyranosid)uronate 在 lithium hydroxide 、 甲基三辛基氯化铵 、 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 benzyl 2,3,4-tri-O-benzyl-α-D-galactopyranosiduronic acid
  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