methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxane-2-carboxylate

• ChemBase编号: 134196
• 分子式: C13H17BrO9
• 平均质量: 397.17268
• 单一同位素质量: 396.00559412
• SMILES: CC(=O)O[C@H]1[C@@H]([C@H](O[C@@H]([C@@H]1OC(=O)C)Br)C(=O)OC)OC(=O)C
• Canonical SMILES: COC(=O)[C@H]1O[C@H](Br)[C@@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C13H17BrO9/c1-5(15)20-8-9(21-6(2)16)11(13(18)19-4)23-12(14)10(8)22-7(3)17/h8-12H,1-4H3/t8-,9-,10+,11-,12-/m0/s1
• InChIKey: GWTNLHGTLIBHHZ-SVNGYHJRSA-N

名称和登记号

名称

• IUPAC标准名: methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxane-2-carboxylate
• IUPAC传统名: methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxane-2-carboxylate
• 别名: (2,3,4-Tri-O-acetyl-α-D-glucopyranosyl bromide)uronic acid methyl ester; Bromo-2,3,4-tri-O-acetyl-α-D-glucopyranuronic acid methyl ester; Methyl acetobromo-α-D-glucuronate; Acetobromo-α-D-glucuronic acid methyl ester; (2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate; 1-Bromo-1-deoxy-2,3,4-triacetate α-D-Glucopyranuronic Acid Methyl Ester; Methyl (Tri-O-acetyl-α-D-glucopyranosyl Bromide)uronate; Methyl 2,3,4-Tri-O-acetyl-1-bromo-1-deoxy-α-D-glucopyranuranate; Methyl α-Acetobromoglucuronate; Acetobromo-α-D-glucuronic Acid Methyl Ester

登记号

• CAS号: 21085-72-3
• EC号: 244-203-4
• MDL号: MFCD00061613
• Beilstein号: 96281
• PubChem SID: 24891328; 162228473; 24845062
• PubChem CID: 88785

理论计算性质

• 质子受体: 5
• 质子供体: 0
• LogD (pH = 5.5): -0.38527408
• LogD (pH = 7.4): -0.38527408
• Log P: -0.38527408
• 摩尔折射率: 74.3686 cm^3
• 极化性: 31.050533 Å^3
• 极化表面积: 114.43 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Chloroform; Dichloromethane; Dimethyl Sulfoxide; Dimethylformamide; Ethyl Acetate; Methaol
• 外观: White Solid
• 熔点: 100-102°C; 80-110 °C(lit.)
• 比旋光度: [α]20/D +190±10°, c = 1% in ethyl acetate

安全信息

• 保存条件: -86°C Freezer
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

产品相关信息

• 纯度: ≥93%; ≥95.0% (GC); 95+%
• 级别: purum
• 运输包装: dry ice
• Empirical Formula (Hill Notation): C13H17BrO9

详细说明

Sigma Aldrich - A8292

Application
Acetobromo-α-D-glucuronic acid methyl ester is used for the synthesis of HMR1098-S-Glucuronide Methyl Ester, a new K-ATP-blocking agent being developed as a drug for prevention of sudden cardiac death.

参考文献

• Honda, T., et al.: J. Med. Chem., 31, 1295 (1988)