1,2:4,6-di-O-isopropylidene-3-O-ter-butyldimethylsilyl-5a-carba-β-L-talopyranose | 457645-33-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2:4,6-di-O-isopropylidene-3-O-ter-butyldimethylsilyl-5a-carba-β-L-talopyranose
• 英文别名: tert-butyl-dimethyl-[[(1S,3S,7S,8R,9R)-5,5,11,11-tetramethyl-4,6,10,12-tetraoxatricyclo[7.4.0.03,7]tridecan-8-yl]oxy]silane
• CAS: 457645-33-9
• 化学式: C₁₉H₃₆O₅Si
• 分子量: 372.577
• InChiKey: QBNDDQPXGMLUOE-ARKGTOAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2:4,6-di-O-isopropylidene-3-O-ter-butyldimethylsilyl-5a-carba-β-L-talopyranose 在 四丁基氟化铵 作用下， 生成 1,2:4,6-di-O-isopropylidene-5a-carba-β-L-talopyranose
  参考文献：
  名称：

  来自 D-甘露糖的 Carbasugars 的立体发散合成。5a-Carba-α-D-alose、β-L-Talose 和 α-L-Gulose Pentaacetates 的合成

  摘要：

  描述了从单一前体到 5a-carba-D-和 L-吡喃糖的立体发散进入。该方法基于多氧化甲基环己烷中间体的选择性脱氧，可从 D-甘露糖衍生物的自由基环化中轻松获得。该策略已应用于 5a-carba-α-D-allo-、5a-carba-β-L-talo-和 5a-carba-α-L-吡喃葡萄糖五乙酸酯的制备。

  DOI：

  10.1055/s-2002-31900
• 作为产物：
  描述：

  1-phenyl-1,2-dideoxy-4,5:6,8-di-O-isopropylidene-D-talo-D-glycero-oct-1-yne 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 偶氮二异丁腈 、 三正丁基氢锡 、 臭氧 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 65.5h， 生成 1,2:4,6-di-O-isopropylidene-3-O-ter-butyldimethylsilyl-5a-carba-β-L-talopyranose
  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

文献信息

• Stereodivergent Synthesis of Carbasugars from D-Mannose. Syntheses of 5a-Carba-α-D-allose, β-L-Talose, and α-L-Gulose Pentaacetates
  作者：Ana M. Gómez、Eduardo Moreno、Serafín Valverde、J. Cristóbal López

  DOI：10.1055/s-2002-31900

  日期：——

  A stereodivergent entry to 5a-carba-D- and L-pyranoses from a single precursor is described. The approach is based on the selective deoxygenation of polyoxygenated methylcyclohexane intermediates, readily available from radical cyclization of D-mannose derivatives. This strategy has been applied to the preparation of 5a-carba-α-D-allo-, 5a-carba-β-L-talo-, and 5a-carba-α-L-gulopyranose pentaacetates

  描述了从单一前体到 5a-carba-D-和 L-吡喃糖的立体发散进入。该方法基于多氧化甲基环己烷中间体的选择性脱氧，可从 D-甘露糖衍生物的自由基环化中轻松获得。该策略已应用于 5a-carba-α-D-allo-、5a-carba-β-L-talo-和 5a-carba-α-L-吡喃葡萄糖五乙酸酯的制备。
• 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
  作者：Ana M. Gómez、Eduardo Moreno、Gerardo O. Danelón、Serafı́n Valverde、J.Cristóbal López

  DOI：10.1016/s0957-4166(03)00532-9

  日期：2003.10

  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.