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

• ChemBase编号: 70278
• 分子式: C13H18O9
• 平均质量: 318.27662
• 单一同位素质量: 318.09508216
• SMILES: [C@@H]1([C@@H]([C@@H]([C@H](O1)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)OC[C@H]1O[C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C13H18O9/c1-6(14)18-5-10-11(19-7(2)15)12(20-8(3)16)13(22-10)21-9(4)17/h10-13H,5H2,1-4H3/t10-,11-,12-,13-/m1/s1
• InChIKey: IHNHAHWGVLXCCI-FDYHWXHSSA-N

名称和登记号

名称

• IUPAC标准名: [(2R,3R,4R,5S)-3,4,5-tris(acetyloxy)oxolan-2-yl]methyl acetate
• IUPAC传统名: [(2R,3R,4R,5S)-3,4,5-tris(acetyloxy)oxolan-2-yl]methyl acetate
• 别名: 1,2,3,5-四-O-乙酰基-β-D-呋喃核糖; β-D-呋喃核糖·1,2,3,5-四乙酸酯; β-D-呋喃核糖1,2,3,5-四乙酸酯; 四乙酰基核糖; β-D-呋喃核糖·1,2,3,5-四-O-乙酸酯; Beta-D-Ribofuranose 1,2,3,5-tetraacetate; 1,2,3,5-Tetra-O-acetyl-β-D-ribofuranose; β-D-Ribofuranose 1,2,3,5-tetraacetate; (2S,3R,4R,5R)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate; 1,2,3,5-Tetra-O-acetyl-beta-D-ribofuranose; beta-D-Ribofuranose 1,2,3,5-tetraacetate; Tetraacetylribose; β-D-Ribofuranose 1,2,3,5-tetra-O-acetate; 1,2,3,5-Tetraacetate β-D-Ribofuranose; β-D-Ribofuranose Tetraacetate; 1,2,3,5-Tetra-O-acetyl-β-D-ribose; 1,2,3,5-Tetraacetyl-β-D-ribofuranose; 1β-D-Tetraacetylribose; NSC 18738; Tetra-O-acetyl-β-D-ribofuranose; Tetraacetyl-β-D-ribofuranose; 1,2,3,5-Tetra-O-acetyl β-D-Ribofuranose

登记号

• CAS号: 13035-61-5
• EC号: 235-898-5
• MDL号: MFCD00005358
• Beilstein号: 94078
• PubChem SID: 162036001; 24849785
• PubChem CID: 83064

理论计算性质

• 质子受体: 5
• 质子供体: 0
• LogD (pH = 5.5): -0.5377026
• LogD (pH = 7.4): -0.5377026
• Log P: -0.5377026
• 摩尔折射率: 66.5669 cm^3
• 极化性: 28.05088 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: Chloroform; Methanol
• 外观: White Solid
• 熔点: 79-82 °C; 80-83°C; 81-83 °C(lit.); 82-84°C
• 比旋光度: [α]20/D -13±0.5°, c = 2.4% in chloroform; [α]26/D -11.4°, c = 10 in chloroform; -13+/-0.5 (c=2.4 in chloroform)

安全信息

• 保存条件: Refrigerator
• 保存注意事项: IRRITANT
• 德国WGK号: 3
• TSCA收录: false; 否
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 纯度: ≥99.0% (TLC); 95+%; 98%; 98+%
• 级别: puriss.
• Empirical Formula (Hill Notation): C13H18O9
• 分类: Derivatives & analogs of Natural Compounds

详细说明

Sigma Aldrich - 159026

Application
核苷合成的原料。
包装
25 g in poly bottle
5 g in glass bottle

Sigma Aldrich - 86560

Other Notes
用于核糖基化的 D-核糖衍生物1,2,3；选择性 1-O-脱乙酰4

Toronto Research Chemicals - T283100

Used in the synthesis of 3-(β-D-ribofuranosyl)-2,3-dihydro-6H-1,3-oxazine-2,6-dione, a new pyrimidine nucleoside analog related to uridine.

参考文献

• Chwang, T.-L., et al.: J. Med. Chem., 19, 643 (1976)