2,4:5,6-Di-O-isopropylidene-1-C-phenyl-D-gluco-hex-1-ulose | 141882-85-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4:5,6-Di-O-isopropylidene-1-C-phenyl-D-gluco-hex-1-ulose
• 英文别名: [(4R,5S,6S)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-hydroxy-2,2-dimethyl-1,3-dioxan-4-yl]-phenylmethanone
• CAS: 141882-85-1
• 化学式: C₁₈H₂₄O₆
• 分子量: 336.385
• InChiKey: VEGVDRRZVOKNJI-BVUBDWEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  0.61
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,4:5,6-Di-O-isopropylidene-1-C-phenyl-D-gluco-hex-1-ulose 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 生成 2,4:5,6-Di-O-isopropylidene-1-C-phenyl-D-glycero-D-ido-hexitol 、 2,4:5,6-Di-O-isopropylidene-1-C-phenyl-D-glycero-D-gulo-hexitol
  参考文献：
  名称：

  Goniofufurone: synthesis and absolute configuration

  摘要：

  通过分子内迈克尔反应这一关键步骤，从 D-甘油-D-古洛-庚酮-γ-内酯毫不含糊地合成出其对映体 1，从而证明天然贡碘呋喃酮的绝对构型为 2。

  DOI：

  10.1039/c39920000432
• 作为产物：
  描述：

  3,5:6,7-bis-O-(1-methylethylidene)-α-D-glucoheptonic γ-lactone 在 sodium tetrahydroborate 、 sodium periodate 、 4 A molecular sieve 、 pyridinium chlorochromate 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 20.0h， 生成 2,4:5,6-Di-O-isopropylidene-1-C-phenyl-D-gluco-hex-1-ulose
  参考文献：
  名称：

  Stereoselective syntheses of 2,4:5,6-di-O-isopropylidene-1 -C-phenyl-D-glycero-D-ido-hexitol and 2,4:5,6-di-O-isopropylidene-1 -C-phenyl-D-glycero-D-gulo-hexitol fromD-glycero-D-gulo-heptono-γ-lactone. X-Ray structure of 1 -O-acetyl-2,4:5,6-di-O-isopropylidene-1-C-phenyl-D-glycero-D-ido-hexitol

  摘要：

  D-glycero-D-gulo-Heptonolactone has been converted by three consecutive reactions (acetonation, reduction and glycol cleavage reaction) into 2,4:5,6-di-O-isopropylidene-D-glucose which with phenylmagnesium bromide gave preponderantly 2,4:5,6-di-O-isopropylidene-1-C-phenyl-D-glycero-D-ido-hexitol 5. 2,4:5,6-Di-O-isopropylidene-1-C-phenyl-D-glycero-D-gulo-hexitol 6 has been obtained from 5 via an oxidation-reduction sequence. The structure of 5 has been confirmed by X-ray crystallographic analysis of its 1-O-acetyl-derivative 12.

  DOI：

  10.1039/p19920000887