2-Hydroxy-1-((3aS,4S,6S,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethanone | 149339-05-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Hydroxy-1-((3aS,4S,6S,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethanone
• CAS: 149339-05-9
• 化学式: C₁₀H₁₆O₆
• 分子量: 232.233
• InChiKey: GYWGGNPLTPTVAA-BGZDPUMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.56
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 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-Hydroxy-1-((3aS,4S,6S,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethanone 在 cation exchange resin AG-50W-X₂ 作用下， 以 水 为溶剂， 反应 10.0h， 以100%的产率得到D-lyxo-hexos-5-ulose
  参考文献：
  名称：

  5-Keto-Mannose (D-Lyxo-Hexos-5-Ulose) in Aqueous Solution-Isomeric Composition Dominated by α/β D-Fructofuranose Related Structures

  摘要：

  Selective C-6 hydroxyl triphenylmethylation of methyl 2,3-O-isopropylidene-alpha-D-mannofuranose (1), followed by C-5 hydroxyl oxidation and sequential removal of protecting groups in aqueous acid, yielded D-lyxo-hexos-5-ulose (5-keto-mannose, 5) as a mixture of isomeric forms. The isomeric mixture of 5 in D2O solution was carefully examined using H-1 and C-13 NMR techniques and structural assignments were made for seven isomers. The most prevalent form of 5 observed was the ketofuranose isomer 2S,5R-D-lyxo-hexo-5,2-furanos-5-ulose 1-hydrate (5a, 52 %), with its 2S,5S-ketofuranose anomer (5b) being the next most abundant (14 %). Also identified in the mixture were the alpha and beta-hexofuranos-5-uloses 5c (6 %) and 5d (< 2 %), the pyranose structure 1R,5R-lyxo-hexopyranos-5-ulose 5e (10 %), and the anhydro isomer 1R,5R-1,6-anhydro-D-lyxo-hexopyranos-5-ulose (5f, 5 %), present in a C-1(4) conformation. Limited spectral information suggests that the remaining isomer 5g (8 %) is a hydrated acyclic aldehyde form of 5.

  DOI：

  10.1080/07328309708005744
• 作为产物：
  描述：

  methyl 2,3-O-isopropylidene-6-O-triphenylmethyl-α-D-mannofuranoside 在 乙酸酐 、 溶剂黄146 、 二甲基亚砜 作用下， 反应 30.0h， 生成 2-Hydroxy-1-((3aS,4S,6S,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethanone
  参考文献：
  名称：

  5-Keto-Mannose (D-Lyxo-Hexos-5-Ulose) in Aqueous Solution-Isomeric Composition Dominated by α/β D-Fructofuranose Related Structures

  摘要：

  Selective C-6 hydroxyl triphenylmethylation of methyl 2,3-O-isopropylidene-alpha-D-mannofuranose (1), followed by C-5 hydroxyl oxidation and sequential removal of protecting groups in aqueous acid, yielded D-lyxo-hexos-5-ulose (5-keto-mannose, 5) as a mixture of isomeric forms. The isomeric mixture of 5 in D2O solution was carefully examined using H-1 and C-13 NMR techniques and structural assignments were made for seven isomers. The most prevalent form of 5 observed was the ketofuranose isomer 2S,5R-D-lyxo-hexo-5,2-furanos-5-ulose 1-hydrate (5a, 52 %), with its 2S,5S-ketofuranose anomer (5b) being the next most abundant (14 %). Also identified in the mixture were the alpha and beta-hexofuranos-5-uloses 5c (6 %) and 5d (< 2 %), the pyranose structure 1R,5R-lyxo-hexopyranos-5-ulose 5e (10 %), and the anhydro isomer 1R,5R-1,6-anhydro-D-lyxo-hexopyranos-5-ulose (5f, 5 %), present in a C-1(4) conformation. Limited spectral information suggests that the remaining isomer 5g (8 %) is a hydrated acyclic aldehyde form of 5.

  DOI：

  10.1080/07328309708005744