prop-2-en-1-yl (3S,4S)-3,4,5,6-tetrahydroxyoxane-2-carboxylate

• ChemBase编号: 159689
• 分子式: C9H14O7
• 平均质量: 234.20326
• 单一同位素质量: 234.07395279
• SMILES: [C@@H]1([C@@H](C(C(OC1C(=O)OCC=C)O)O)O)O
• Canonical SMILES: C=CCOC(=O)C1OC(O)C([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C9H14O7/c1-2-3-15-9(14)7-5(11)4(10)6(12)8(13)16-7/h2,4-8,10-13H,1,3H2/t4-,5-,6?,7?,8?/m0/s1
• InChIKey: HYPHSXHTCHCXAT-VOICCNKESA-N

名称和登记号

名称

• IUPAC标准名: prop-2-en-1-yl (3S,4S)-3,4,5,6-tetrahydroxyoxane-2-carboxylate
• IUPAC传统名: prop-2-en-1-yl (3S,4S)-3,4,5,6-tetrahydroxyoxane-2-carboxylate
• 别名: D-Glucopyranuronic Acid 2-Propen-1-yl Ester; D-Glucuronic Acid 2-Propenyl Ester; Allyl D-Glucuronate

登记号

• CAS号: 188717-04-6
• PubChem SID: 162253824
• PubChem CID: 46780125

理论计算性质

• Acid pKa: 11.283208
• 质子受体: 6
• 质子供体: 4
• LogD (pH = 5.5): -1.7351215
• LogD (pH = 7.4): -1.7351775
• Log P: -1.7351208
• 摩尔折射率: 49.7226 cm^3
• 极化性: 20.550245 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: DMF; Ethanol; Methanol; Water
• 外观: White to Off-White Solid
• 熔点: 126-128°C

安全信息

• 保存条件: -86°C Freezer, Under Inert Atmosphere

详细说明

Toronto Research Chemicals - A555400

It is used in efficient synthesis of 1β-O-acyl glucuronides via regioselective acylation of allyl or benzyl D-glucuronate.Αcyl glucuronides are known metabolites of important drugs.

参考文献

• Kaspersen, F., et al.: Xenobiotica, 17, 1451 (1987)
• Ebner, T., et al.: Drug Metab. Dispos., 27, 1143 (1987)
• Shipkova, M., et al.: Ther. Drug Monit., 25, 1 (1987)
• Stachulski, A., et al.: J. Med. Chem., 49, 6931 (1987)