| 177568-26-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• CAS: 177568-26-2
• 化学式: C₁₅H₂₄O₉
• 分子量: 348.35
• InChiKey: XWBMKZTVEHDVDB-NLDQXQBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.72
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  112.91
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到(1S,2R)-1-((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-yl)-propane-1,2,3-triol
  参考文献：
  名称：

  Synthesis of 4-Octuloses from a Derivative ofd-Fructose

  摘要：

  Reaction of 2,3:4,5-di-O-isopropylidene-beta-D-arabino-hexos-2-ulo-2,6-pyranose (1) with (methoxycarbonylmethylene)triphenylphosphorane in either dichloromethane or methanol gave methyl (E)-2,3-dideoxy-4,5:6,7-di-O-isopropylidene-beta-D-arabino-oct-2-ene-4-ulo-4,8-pyranosonate (2) or a 1:2.3 mixture of 2 and its Z-isomer (3), respectively. Bishydroxylation of 2 with osmium tetraoxide gave a mixture of methyl 4,5:6,7-di-O-isopropylidene-beta-D-glycero-D-galacto- (4) and -D-glycero-D-ido-oct-4-ulo-4,8-pyranosonate (5) which were carefully resolved by column chromatography. Compound 4 was transformed into its 2,3-di-O-methyl derivative (6) which was deacetonated to 7 and subsequently degraded to dimethyl 2,3-di-O-methyl-(+/-)-L-tartrate (8). On the other hand, acetonation of a mixture of 4 and 5 gave the corresponding tri-O-isopropylidene derivatives (9) and (10). Compounds 4 and 5 were reduced with LiAlH4 to the related 4,5:6,7-di-O-isopropylidene-beta-D-glycero-D-galacto- (11) and -beta-D-glycero-D-ido-oct-4-ulo-4,8-pyranose (12). Treatment of 11 and 12 with acetone/PTSA/CuSO4 only produced the acetonation at the C-2,3 positions. Finally, compounds 11 and 12 were deacetonated to the corresponding D-glycero-D-galacto- (15) and D-glycero-D-ido-oct-4-ulose (16).

  DOI：

  10.1080/07328309608005655
• 作为产物：
  描述：

  2,3:4,5-bis-O-(isopropylidene)-D-fructopyranose aldehyde 在 四氧化锇 、 potassium chlorate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Synthesis of 4-Octuloses from a Derivative ofd-Fructose

  摘要：

  Reaction of 2,3:4,5-di-O-isopropylidene-beta-D-arabino-hexos-2-ulo-2,6-pyranose (1) with (methoxycarbonylmethylene)triphenylphosphorane in either dichloromethane or methanol gave methyl (E)-2,3-dideoxy-4,5:6,7-di-O-isopropylidene-beta-D-arabino-oct-2-ene-4-ulo-4,8-pyranosonate (2) or a 1:2.3 mixture of 2 and its Z-isomer (3), respectively. Bishydroxylation of 2 with osmium tetraoxide gave a mixture of methyl 4,5:6,7-di-O-isopropylidene-beta-D-glycero-D-galacto- (4) and -D-glycero-D-ido-oct-4-ulo-4,8-pyranosonate (5) which were carefully resolved by column chromatography. Compound 4 was transformed into its 2,3-di-O-methyl derivative (6) which was deacetonated to 7 and subsequently degraded to dimethyl 2,3-di-O-methyl-(+/-)-L-tartrate (8). On the other hand, acetonation of a mixture of 4 and 5 gave the corresponding tri-O-isopropylidene derivatives (9) and (10). Compounds 4 and 5 were reduced with LiAlH4 to the related 4,5:6,7-di-O-isopropylidene-beta-D-glycero-D-galacto- (11) and -beta-D-glycero-D-ido-oct-4-ulo-4,8-pyranose (12). Treatment of 11 and 12 with acetone/PTSA/CuSO4 only produced the acetonation at the C-2,3 positions. Finally, compounds 11 and 12 were deacetonated to the corresponding D-glycero-D-galacto- (15) and D-glycero-D-ido-oct-4-ulose (16).

  DOI：

  10.1080/07328309608005655