3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-1,2-dideoxy-β-1-phenyl-D-ribofuranose | 137616-57-0

• 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: 3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-1,2-dideoxy-β-1-phenyl-D-ribofuranose
• 英文别名: (6aR,8R,9aS)-8-phenyl-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocine
• CAS: 137616-57-0
• 化学式: C₂₃H₄₀O₄Si₂
• 分子量: 436.739
• InChiKey: SBYHSKSZHMTGGK-XPWALMASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.47
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-1,2-dideoxy-β-1-phenyl-D-ribofuranose 在 氢氟酸 作用下， 生成 1,2-二脱氧-1-苯基-beta-呋喃核糖
  参考文献：
  名称：

  Erythrose sesqui-acetals as electrophiles. 2-Deoxy-C-nucleosides from D-glucose.

  摘要：

  Cleavage of glucosides with NalO4 in MeOH furnishes sesqui-acetals (protected dialdehydes). Olefination of these substrates, followed by endocyclic oxymercuration-demercuration furnishes substituted tetrahydrofurans (1,2-dideoxy-1-aryl-D-ribofuranoses). Proper choice of protecting groups can affect the face selectivity of the oxymercuration step to provide only the desired beta-C-anomer.

  DOI：

  10.1016/s0040-4039(00)93472-5
• 作为产物：
  描述：

  Methyl 4,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-dily)-α-D-glucopyranoside 在 盐酸 、 sodium tetrahydroborate 、 sodium iodate 、 mercury(II) diacetate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 生成 3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-1,2-dideoxy-β-1-phenyl-D-ribofuranose
  参考文献：
  名称：

  Erythrose sesqui-acetals as electrophiles. 2-Deoxy-C-nucleosides from D-glucose.

  摘要：

  Cleavage of glucosides with NalO4 in MeOH furnishes sesqui-acetals (protected dialdehydes). Olefination of these substrates, followed by endocyclic oxymercuration-demercuration furnishes substituted tetrahydrofurans (1,2-dideoxy-1-aryl-D-ribofuranoses). Proper choice of protecting groups can affect the face selectivity of the oxymercuration step to provide only the desired beta-C-anomer.

  DOI：

  10.1016/s0040-4039(00)93472-5

文献信息

• Erythrose sesqui-acetals as electrophiles. 2-Deoxy-C-nucleosides from D-glucose.
  作者：Robin Polt、Thusitha Wijayarathe

  DOI：10.1016/s0040-4039(00)93472-5

  日期：1991.9

  Cleavage of glucosides with NalO4 in MeOH furnishes sesqui-acetals (protected dialdehydes). Olefination of these substrates, followed by endocyclic oxymercuration-demercuration furnishes substituted tetrahydrofurans (1,2-dideoxy-1-aryl-D-ribofuranoses). Proper choice of protecting groups can affect the face selectivity of the oxymercuration step to provide only the desired beta-C-anomer.
• Disiloxane-Protected 2-Deoxyribonolactone as an Efficient Precursor to 1,2-Dideoxy-1-β-aryl-<scp>d</scp>-ribofuranoses
  作者：Uthai Wichai、Stephen A. Woski

  DOI：10.1021/ol990813w

  日期：1999.10.1

  [GRAPHICS]Aryl C-nucleosides are analogues of natural nucleosides where the bases have been replaced with aromatic moieties, Work herein describes the highly stereoselective syntheses of non-hydrogen-bonding carbocyclic derivatives using a disiloxane-protected 2-deoxy-D-ribono-1,4-lactone as a stable and readily accessible starting material. Unlike the bis(TBDMS)-protected congener, this compound enables the use of sterically congested ortho-substituted aryllithium reagents in the initial addition reaction.