(2S,3R,4R)-1-O,4-O,5-O-tribenzyl-L-xylitol | 173397-75-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3R,4R)-1-O,4-O,5-O-tribenzyl-L-xylitol
• 英文别名: (2S,3R,4R)-1,4,5-tris(phenylmethoxy)pentane-2,3-diol
• CAS: 173397-75-6
• 化学式: C₂₆H₃₀O₅
• 分子量: 422.521
• InChiKey: NBBSEWQCCGTVME-JIMJEQGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-methoxytrifluoromethylphenylacetyl chloride 、 (2S,3R,4R)-1-O,4-O,5-O-tribenzyl-L-xylitol 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 1.5h， 生成 (2S,3S,4R)-1-O,4-O,5-O-tribenzyl-2-O,3-O-di((R)-α-methoxy-α-(trifluoromethyl)phenylacetyl)-xylitol
  参考文献：
  名称：

  Dispiroketals in synthesis (part 19)1: Dispiroketals as enantioselective and regioselective protective agents for symmetric cyclic and acyclic polyols.

  摘要：

  The enantioselective preparation of both enantiomers of a C-2-symmetric diphenyl-bi-dihydropyran 3 and 4 is described. The application of enantiopure bi-dihydropyrans 1 - 4 towards the simultaneous enantioselective differentiation and regioselective protection of a range of cyclic and acyclic symmetrical polyols (23, 37, 43, 45, 54, 61 and 66) is investigated. Several deprotections utilising trifluoroacetic acid (TFA) and a transketalisation with acidic glycerol are presented.

  DOI：

  10.1016/0957-4166(95)00318-j
• 作为产物：
  描述：

  (2S,2'R,2''R,3S,4S,6'S,6''S)-2-O,3-O-(6,6'-dimethyl-3,3',4,4',5,5',6,6'-octahydro-2,2'-bi-2H-pyran-2,2'-diyl)-xylitol 在 四丁基碘化铵 、 sodium hydride 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 (2S,3R,4R)-1-O,4-O,5-O-tribenzyl-L-xylitol
  参考文献：
  名称：

  Dispiroketals in synthesis (part 19)1: Dispiroketals as enantioselective and regioselective protective agents for symmetric cyclic and acyclic polyols.

  摘要：

  The enantioselective preparation of both enantiomers of a C-2-symmetric diphenyl-bi-dihydropyran 3 and 4 is described. The application of enantiopure bi-dihydropyrans 1 - 4 towards the simultaneous enantioselective differentiation and regioselective protection of a range of cyclic and acyclic symmetrical polyols (23, 37, 43, 45, 54, 61 and 66) is investigated. Several deprotections utilising trifluoroacetic acid (TFA) and a transketalisation with acidic glycerol are presented.

  DOI：

  10.1016/0957-4166(95)00318-j

文献信息

• Dispiroketals in synthesis (part 19)1: Dispiroketals as enantioselective and regioselective protective agents for symmetric cyclic and acyclic polyols.
  作者：Robert Downham、Paul J Edwards、David A Entwistle、Andrew B Hughes、Kun Soo Kim、Steven V Ley

  DOI：10.1016/0957-4166(95)00318-j

  日期：1995.10

  The enantioselective preparation of both enantiomers of a C-2-symmetric diphenyl-bi-dihydropyran 3 and 4 is described. The application of enantiopure bi-dihydropyrans 1 - 4 towards the simultaneous enantioselective differentiation and regioselective protection of a range of cyclic and acyclic symmetrical polyols (23, 37, 43, 45, 54, 61 and 66) is investigated. Several deprotections utilising trifluoroacetic acid (TFA) and a transketalisation with acidic glycerol are presented.