(4R,5R)-4-[(4R,5R)-5-((S)-1-Hydroxy-3-phenyl-prop-2-ynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2,2-dimethyl-[1,3]dioxan-5-ol | 631917-85-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-4-[(4R,5R)-5-((S)-1-Hydroxy-3-phenyl-prop-2-ynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2,2-dimethyl-[1,3]dioxan-5-ol
• CAS: 631917-85-6
• 化学式: C₂₀H₂₆O₆
• 分子量: 362.423
• InChiKey: ABDVIJJGJNMZNZ-YYWYGQEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.43
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (4R,5R)-4-[(4R,5R)-5-((S)-1-Hydroxy-3-phenyl-prop-2-ynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2,2-dimethyl-[1,3]dioxan-5-ol 在 吡啶 、 4-二甲氨基吡啶 、 氢氟酸 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.0h， 生成 Carbonic acid (S)-1-[(4R,5R)-5-((4R,5R)-2,2-dimethyl-5-phenoxythiocarbonyloxy-[1,3]dioxan-4-yl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-phenyl-prop-2-ynyl ester ethyl ester
  参考文献：
  名称：

  Stereodivergent synthesis of 5a-carba-hexopyranoses from carbohydrates via 6-exo-dig radical cyclization: preparation of 5a-carba-β-d-manno-, α-d-allo-, β-l-talo- and α-l-gulopyranose pentaacetates from d-mannose

  摘要：

  Four carbasugars. 5a-carba-beta-D-manno-, alpha-D-allo-, beta-L-talo- and alpha-L-gulopyranose pentaacetates, have been prepared in a stereodivergent manner from D-mannose. Alkynyl derivatives of 2,3:4,6-di-O-isopropylidene-D-mannopyranose, which are prepared by homologation at C-1. by reaction with phenyl acetylide, undergo a 6-exo-dig radical cyclization, from a radical located at C-5. to yield a mixture of highly functionalized cyclohexanes. Some of these compounds, after transformation of their exocyclic double bond in a hydroxy function, were correlated with polyhydroxylated cyclohexanes, which were then selectively deoxygenated either at position C-4 or C-5a (carbohydrate numbering) to afford carbasugars of the D- Or L- series. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00532-9
• 作为产物：
  描述：

  2,3:4,6-di-O-isopropylidene-D-mannopyranose 、 苯乙炔 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以57%的产率得到1-phenyl-1,2-dideoxy-4,5:6,8-di-O-isopropylidene-D-talo-D-glycero-oct-1-yne
  参考文献：
  名称：

  Stereodivergent synthesis of 5a-carba-hexopyranoses from carbohydrates via 6-exo-dig radical cyclization: preparation of 5a-carba-β-d-manno-, α-d-allo-, β-l-talo- and α-l-gulopyranose pentaacetates from d-mannose

  摘要：

  Four carbasugars. 5a-carba-beta-D-manno-, alpha-D-allo-, beta-L-talo- and alpha-L-gulopyranose pentaacetates, have been prepared in a stereodivergent manner from D-mannose. Alkynyl derivatives of 2,3:4,6-di-O-isopropylidene-D-mannopyranose, which are prepared by homologation at C-1. by reaction with phenyl acetylide, undergo a 6-exo-dig radical cyclization, from a radical located at C-5. to yield a mixture of highly functionalized cyclohexanes. Some of these compounds, after transformation of their exocyclic double bond in a hydroxy function, were correlated with polyhydroxylated cyclohexanes, which were then selectively deoxygenated either at position C-4 or C-5a (carbohydrate numbering) to afford carbasugars of the D- Or L- series. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00532-9