(2R,3S,4R,5R)-2,3-bis(acetyloxy)-6,8-dioxabicyclo[3.2.1]octan-4-yl acetate

• ChemBase编号: 160675
• 分子式: C12H16O8
• 平均质量: 288.25064
• 单一同位素质量: 288.08451747
• SMILES: [C@@H]1([C@@H]([C@@H]([C@H]2OC1CO2)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)O[C@H]1[C@H](OC(=O)C)C2CO[C@@H]([C@H]1OC(=O)C)O2
• InChI: InChI=1S/C12H16O8/c1-5(13)17-9-8-4-16-12(20-8)11(19-7(3)15)10(9)18-6(2)14/h8-12H,4H2,1-3H3/t8?,9-,10+,11-,12-/m1/s1
• InChIKey: BAKQMOSGYGQJOJ-UPUXHGCUSA-N

名称和登记号

名称

• IUPAC标准名: (2R,3S,4R,5R)-2,3-bis(acetyloxy)-6,8-dioxabicyclo[3.2.1]octan-4-yl acetate
• IUPAC传统名: (2R,3S,4R,5R)-2,3-bis(acetyloxy)-6,8-dioxabicyclo[3.2.1]octan-4-yl acetate
• 别名: 2,3,4-Tri-O-acetyl-1,6-anhydro-β-D-glucopyranose; Triacetyllevoglucosan; NSC 25284; 1,6-Anhydro-β-D-glucopyranose 2,3,4-Triacetate

登记号

• CAS号: 13242-55-2
• PubChem SID: 162254810
• PubChem CID: 71313422

理论计算性质

• 质子受体: 5
• 质子供体: 0
• LogD (pH = 5.5): -0.44745943
• LogD (pH = 7.4): -0.44745943
• Log P: -0.44745943
• 摩尔折射率: 59.8678 cm^3
• 极化性: 25.374388 Å^3
• 极化表面积: 97.36 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO; Methanol
• 外观: White Solid
• 熔点: 108-109°C

安全信息

• 保存条件: -20°C Freezer

详细说明

Toronto Research Chemicals - A648200

1,6-Anhydrohexopyranoses have proven to be valuable synthons for the preparation of biologically important and structurally diverse products (e.g. rifamycin S, indanomycin, thromboxane B2, (+)-biotin, tetrodotoxin, quinone, and macrolide antibiotics) as

参考文献

• Fraser-Reid, B., et al. J. Am. Chem. Soc. 106, 731 (1984)
• Edwards, M.P., et al. J. Org. Chem. 49, 3503 (1984)
• Kelly, A.G., and Roberts, J.S. J. Chem. Soc., Chem. Commun. 228, (1984)
• Ogawa, T., et al. Carbohydr. Res. 57, C31 (1984)
• Isobe, M., et al. Te