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

• ChemBase编号: 102911
• 分子式: C28H24O9
• 平均质量: 504.48476
• 单一同位素质量: 504.14203235
• SMILES: O=C(O[C@@H]1O[C@@H]([C@@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1)COC(=O)c1ccccc1)C
• Canonical SMILES: CC(=O)O[C@@H]1O[C@@H]([C@H]([C@H]1OC(=O)c1ccccc1)OC(=O)c1ccccc1)COC(=O)c1ccccc1
• InChI: InChI=1S/C28H24O9/c1-18(29)34-28-24(37-27(32)21-15-9-4-10-16-21)23(36-26(31)20-13-7-3-8-14-20)22(35-28)17-33-25(30)19-11-5-2-6-12-19/h2-16,22-24,28H,17H2,1H3/t22-,23-,24-,28-/m1/s1
• InChIKey: GCZABPLTDYVJMP-CBUXHAPBSA-N

名称和登记号

名称

• IUPAC标准名: (2R,3R,4R,5S)-5-(acetyloxy)-4-(benzoyloxy)-2-[(benzoyloxy)methyl]oxolan-3-yl benzoate; (2S,3R,4R,5R)-2-(acetyloxy)-4-(benzoyloxy)-5-[(benzoyloxy)methyl]oxolan-3-yl benzoate; [(2R,3R,4R,5S)-5-(acetyloxy)-3,4-bis(benzoyloxy)oxolan-2-yl]methyl benzoate
• IUPAC传统名: (2R,3R,4R,5S)-5-(acetyloxy)-4-(benzoyloxy)-2-[(benzoyloxy)methyl]oxolan-3-yl benzoate; (2S,3R,4R,5R)-2-(acetyloxy)-4-(benzoyloxy)-5-[(benzoyloxy)methyl]oxolan-3-yl benzoate; [(2R,3R,4R,5S)-5-(acetyloxy)-3,4-bis(benzoyloxy)oxolan-2-yl]methyl benzoate
• 别名: 1-O-乙酰基-2,3,5-三-O-苯甲酰基-β-D-呋喃核糖; 1-乙酰氧基-2,3,5-三苯甲酰氧基-1-β-D-呋喃核糖; 1-乙酰基-2,3,5-三苯甲酰基-β-D-呋喃核糖; 1-O-乙酰基-2,3,5-O-三苯甲酰基-β-D-呋喃核糖; 1-Acetyl-2,3,5-tribenzoyl-β-D-ribofuranoside; β-D-Ribofuranose 1-acetate 2,3,5-tribenzoate; 1-O-ACETYL-2,3,5-TRIBENZOYL-β-D-RIBOFURANOSIDE; 1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose; β-D-Ribofuranose 1-acetate 2,3,5-tribenzoate; beta-D-Ribofuranose 1-Acetate 2,3,5-Tribenzoate; β-D-Ribofuranose 1-acetate 2,3,5-tribenzoate; β-D-Ribofuranose 1-Αcetate 2,3,5-Tribenzoate; 1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribose; 2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl Acetate; ABR; NSC 23349; 1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose; 1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose; 1-ACETYL-2,3,5-TRIBENZOYL-β-D-RIBOFURANOSE; 1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose; 2,3,5-TRI-O-BENZOYL-1-O-ACETYL-β-D-RIBOFURANOSE

登记号

• CAS号: 6974-32-9
• EC号: 230-220-4
• MDL号: MFCD00005357
• Beilstein号: 100243
• PubChem SID: 162091287; 24844890; 24849784
• PubChem CID: 81455

理论计算性质

• 质子受体: 5
• 质子供体: 0
• LogD (pH = 5.5): 5.6248207
• LogD (pH = 7.4): 5.6248207
• Log P: 5.6248207
• 摩尔折射率: 128.5784 cm^3
• 极化性: 50.93317 Å^3
• 极化表面积: 114.43 Å^2
• 可自由旋转的化学键: 12
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: Chloroform; Methanol; Pyridine
• 外观: White Solid
• 熔点: 128-130 °C; 128-130 °C(lit.); 128-130°C; 128-130°C
• 比旋光度: [α]20/D +24.3°, c = 1 in pyridine; [α]20/D +44±1°, c = 0.5% in chloroform

安全信息

• 保存条件: -20°C Freezer; Room Temperature (15-30°C)
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 纯度: ≥97.0% (TLC); 98%
• 级别: purum
• Empirical Formula (Hill Notation): C28H24O9

详细说明

MP Biomedicals - 02105455

Crystalline
An important intermediate in the chemical synthesis of ribonucleosides.

MP Biomedicals - 05206427

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 159018

Application
核苷合成的原料。
包装
1, 10 g in glass bottle

Sigma Aldrich - 01510

Other Notes
核糖衍生物，用于核苷的合成1,2,3,4；与 Me3SiC 产生 1-氰化反应

Toronto Research Chemicals - A189330

An inhibitor of neutrophil-keyhole limpet hemocyanin adhesion. Anti-inflammatory agent.

参考文献

• Shappell, S., et al.: J. Immunol., 144, 2702 (1990)
• Ross, L., et al.: J. Biol. Chem., 267, 8537 (1990)
• Granger, D., et al.: J. Leukoc. Biol., 55, 662 (1990)