(R)-2-Benzyloxy-3-[(3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-propionaldehyde | 153941-93-6

• 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: (R)-2-Benzyloxy-3-[(3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-propionaldehyde
• CAS: 153941-93-6
• 化学式: C₂₂H₃₀O₇
• 分子量: 406.476
• InChiKey: GSBAOFBOKCCHLN-BGSOWLKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (R)-2-Benzyloxy-3-[(3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-propionaldehyde 在 silver(l) oxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 为溶剂， 反应 14.0h， 生成 (R)-2-Benzyloxy-3-[(3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-propionic acid methyl ester
  参考文献：
  名称：

  C-glycofuranosides via tandem Wittig-Michael sequence using a thiazole-armed phosphorane. A route to C-furanosyl α-hydroxy propanals and propionic acids

  摘要：

  The reactions of 2-thiazolylcarbonylmethylenetriphenylphosphorane with five protected D-furanoses (manno, ribo, arabino, xylo, and lyxo) in refluxing toluene lead to mixtures of alpha- and beta-1-C-(2-thiazolacyl)-glycosides (66 - 93 % overall yield). The beta-linked C-glycoside derived from 2,3:5,6-di-O-isopropylidene-D-mannofuranose was reduced to (R) and (S) alcohols which after protection as O-benzyl ethers were transformed to alpha-alkoxy aldehydes by thiazole-to-formyl conversion; the aldehydes were oxidized to the corresponding alpha-alkoxy acids.

  DOI：

  10.1016/s0040-4039(00)79321-x
• 作为产物：
  描述：

  2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 在 sodium tetrahydroborate 、 4 A molecular sieve 、 sodium hydride 、 lithium tri-t-butoxyaluminum hydride 、 三氟甲烷磺酸甲酯 、 copper(II) oxide 、 copper dichloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 25.5h， 生成 (R)-2-Benzyloxy-3-[(3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-propionaldehyde
  参考文献：
  名称：

  C-glycofuranosides via tandem Wittig-Michael sequence using a thiazole-armed phosphorane. A route to C-furanosyl α-hydroxy propanals and propionic acids

  摘要：

  The reactions of 2-thiazolylcarbonylmethylenetriphenylphosphorane with five protected D-furanoses (manno, ribo, arabino, xylo, and lyxo) in refluxing toluene lead to mixtures of alpha- and beta-1-C-(2-thiazolacyl)-glycosides (66 - 93 % overall yield). The beta-linked C-glycoside derived from 2,3:5,6-di-O-isopropylidene-D-mannofuranose was reduced to (R) and (S) alcohols which after protection as O-benzyl ethers were transformed to alpha-alkoxy aldehydes by thiazole-to-formyl conversion; the aldehydes were oxidized to the corresponding alpha-alkoxy acids.

  DOI：

  10.1016/s0040-4039(00)79321-x