benzyl (3S,5S)-3,4,5,6-tetrahydroxyoxane-2-carboxylate

• ChemBase编号: 161608
• 分子式: C13H16O7
• 平均质量: 284.26194
• 单一同位素质量: 284.08960285
• SMILES: O1C([C@@H](C([C@@H](C1C(=O)OCc1ccccc1)O)O)O)O
• Canonical SMILES: OC1OC(C(=O)OCc2ccccc2)[C@H](C([C@H]1O)O)O
• InChI: InChI=1S/C13H16O7/c14-8-9(15)11(20-12(17)10(8)16)13(18)19-6-7-4-2-1-3-5-7/h1-5,8-12,14-17H,6H2/t8?,9-,10-,11?,12?/m0/s1
• InChIKey: MYEUFSLWFIOAGY-SJZSRGDHSA-N

名称和登记号

名称

• IUPAC标准名: benzyl (3S,5S)-3,4,5,6-tetrahydroxyoxane-2-carboxylate
• IUPAC传统名: benzyl (3S,5S)-3,4,5,6-tetrahydroxyoxane-2-carboxylate
• 别名: Glucuronic Acid Benzyl Ester; D-Glucuronic Acid Phenylmethyl Ester; Benzyl D-Glucuronate

登记号

• CAS号: 135970-30-8
• PubChem SID: 162255743
• PubChem CID: 45038287

理论计算性质

• Acid pKa: 11.283208
• 质子受体: 6
• 质子供体: 4
• LogD (pH = 5.5): -0.74189824
• LogD (pH = 7.4): -0.74195427
• Log P: -0.7418975
• 摩尔折射率: 65.1725 cm^3
• 极化性: 26.588284 Å^3
• 极化表面积: 116.45 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO; Methanol; Water
• 外观: White to Off-White Solid
• 熔点: 104-108°C

安全信息

• 保存条件: -20°C Freezer, Under Inert Atmosphere

详细说明

Toronto Research Chemicals - B279800

Used in efficient synthesis of 1β-O-acyl glucuronides via regioselective acylation

参考文献

• Meng, X., et al.: J. Med. Chem., 50, 6165 (2007)