methyl 2-[(2R,3S,5R)-3-[tert-butyl(diphenyl)silyl]oxy-5-methoxyoxolan-2-yl]prop-2-enoate | 161363-96-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-[(2R,3S,5R)-3-[tert-butyl(diphenyl)silyl]oxy-5-methoxyoxolan-2-yl]prop-2-enoate
• CAS: 161363-96-8
• 化学式: C₂₅H₃₂O₅Si
• 分子量: 440.612
• InChiKey: MQCIDKPOLYNZOD-YTFSRNRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-[(2R,3S,5R)-3-[tert-butyl(diphenyl)silyl]oxy-5-methoxyoxolan-2-yl]prop-2-enoate 在 4-二甲氨基吡啶 、 叔丁基二甲硅基三氟甲磺酸酯 、 四丁基氟化铵 、 氨 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-[(2R,4S,5R)-4-hydroxy-5-(3-hydroxyprop-1-en-2-yl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of a nucleoside analog bearing a branched difunctional sidechain using the palladium-mediated cyclization of a γ-oxoallene

  摘要：

  The aldehyde 8 was synthesized in high yield and with excellent stereoselectivity by treating a protected 3-hydroxypropanal with Corey's chiral B-propargyl boradiazoline reagent. Cyclization of this gamma-oxoallene with palladium(II) in the presence of methanol and carbon monoxide produced the furanoside 9 with excellent stereoselectivity for the D-deoxyribose geometry. The furanoside 9 was converted to the branched extended sidechain deoxythymidine analog 11 by reduction, protection, and beta-stereoselective Vorbruggen coupling. The hydroboration/oxidation of 10 to yield the deoxyribofuranoside analog 13, bearing two sidechain hydroxyl groups, was also demonstrated.

  DOI：

  10.1016/s0040-4039(00)78432-2
• 作为产物：
  描述：

  在 pyridinium chlorochromate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 生成 methyl 2-[(2R,3S,5R)-3-[tert-butyl(diphenyl)silyl]oxy-5-methoxyoxolan-2-yl]prop-2-enoate
  参考文献：
  名称：

  Synthesis of a nucleoside analog bearing a branched difunctional sidechain using the palladium-mediated cyclization of a γ-oxoallene

  摘要：

  The aldehyde 8 was synthesized in high yield and with excellent stereoselectivity by treating a protected 3-hydroxypropanal with Corey's chiral B-propargyl boradiazoline reagent. Cyclization of this gamma-oxoallene with palladium(II) in the presence of methanol and carbon monoxide produced the furanoside 9 with excellent stereoselectivity for the D-deoxyribose geometry. The furanoside 9 was converted to the branched extended sidechain deoxythymidine analog 11 by reduction, protection, and beta-stereoselective Vorbruggen coupling. The hydroboration/oxidation of 10 to yield the deoxyribofuranoside analog 13, bearing two sidechain hydroxyl groups, was also demonstrated.

  DOI：

  10.1016/s0040-4039(00)78432-2

文献信息

• Synthesis of a nucleoside analog bearing a branched difunctional sidechain using the palladium-mediated cyclization of a γ-oxoallene
  作者：Robert D. Walkup、Michael D. Mosher

  DOI：10.1016/s0040-4039(00)78432-2

  日期：1994.11

  The aldehyde 8 was synthesized in high yield and with excellent stereoselectivity by treating a protected 3-hydroxypropanal with Corey's chiral B-propargyl boradiazoline reagent. Cyclization of this gamma-oxoallene with palladium(II) in the presence of methanol and carbon monoxide produced the furanoside 9 with excellent stereoselectivity for the D-deoxyribose geometry. The furanoside 9 was converted to the branched extended sidechain deoxythymidine analog 11 by reduction, protection, and beta-stereoselective Vorbruggen coupling. The hydroboration/oxidation of 10 to yield the deoxyribofuranoside analog 13, bearing two sidechain hydroxyl groups, was also demonstrated.