[(2R,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate

• ChemBase编号: 92225
• 分子式: C14H19BrO9
• 平均质量: 411.19926
• 单一同位素质量: 410.02124419
• SMILES: Br[C@H]1O[C@@H]([C@H](OC(=O)C)[C@H](OC(=O)C)[C@H]1OC(=O)C)COC(=O)C
• Canonical SMILES: CC(=O)OC[C@H]1O[C@H](Br)[C@@H]([C@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C14H19BrO9/c1-6(16)20-5-10-11(21-7(2)17)12(22-8(3)18)13(14(15)24-10)23-9(4)19/h10-14H,5H2,1-4H3/t10-,11+,12+,13-,14+/m1/s1
• InChIKey: CYAYKKUWALRRPA-HTOAHKCRSA-N

名称和登记号

名称

• IUPAC标准名: [(2R,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate
• IUPAC传统名: [(2R,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate
• 别名: 2,3,4,6-Tetra-O-acetyl-α-D-galactopyranosyl bromide; Acetobromo-α-D-galactose; 2,3,4,6-Tetra-O-acetyl-a-D-galactopyranosyl bromide; Acetobromo-α-D-Galactose; Acetobromogalactose; Bromo 2,3,4,6-Tetra-O-acetyl-α-D-galactopyranoside; Acetobromo-a-D-galactose; Bromo-2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranose

登记号

• CAS号: 3068-32-4
• MDL号: MFCD00063686
• Beilstein号: 96671
• PubChem SID: 162078923; 24845060; 24891250
• PubChem CID: 2734143

理论计算性质

• 质子受体: 5
• 质子供体: 0
• LogD (pH = 5.5): -0.3887714
• LogD (pH = 7.4): -0.3887714
• Log P: -0.3887714
• 摩尔折射率: 78.8836 cm^3
• 极化性: 32.837383 Å^3
• 极化表面积: 114.43 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Dichloromethane
• 外观: White Crystalline Solid
• 熔点: 82-83°C
• 比旋光度: [α]20/D +205±10°, c = 3% in chloroform

安全信息

• 保存条件: -20°C Freezer, Under Inert Atmosphere
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: -20°C

产品相关信息

• 纯度: ≥90% (AT); ≥93% (TLC); 95+%
• 级别: technical
• 其他组分: ~1% CaCO3 as stabilizer; 1% CaCO3 as stabilizer
• 运输包装: dry ice; wet ice
• Empirical Formula (Hill Notation): C14H19BrO9

详细说明

Sigma Aldrich - A7562

Application
2,3,4,6-Tetra-O-acetyl-α-D-galactopyranosyl bromide is used as an organic condensation reagent for chemistries such as N- and S- galactosylation reactions and the synthesis of spacer-equipped phosphorylated di-, tri- and tetrasaccharide fragments of the O-specific polysaccharides.

Sigma Aldrich - 00525

Other Notes
Galactose derivative used for the β-galactosylation of alcohols (Königs-Knorr synthesis)1,2; Preparation of tri-O-acetylgalactal3

Toronto Research Chemicals - B687000

Temperature and moisture sensitive; Store in freezer; Stabilized with 2% CaCO3