(3S,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]oxolan-2-yl 4-nitrobenzoate

• ChemBase ID: 138824
• Molecular Formular: C33H31NO8
• Molecular Mass: 569.60114
• Monoisotopic Mass: 569.20496696
• SMILES: c1ccc(cc1)COC[C@@H]1[C@H]([C@@H](C(O1)OC(=O)c1ccc(cc1)[N+](=O)[O-])OCc1ccccc1)OCc1ccccc1
• Canonical SMILES: O=C(c1ccc(cc1)[N+](=O)[O-])OC1O[C@@H]([C@H]([C@@H]1OCc1ccccc1)OCc1ccccc1)COCc1ccccc1
• InChI: InChI=1S/C33H31NO8/c35-32(27-16-18-28(19-17-27)34(36)37)42-33-31(40-22-26-14-8-3-9-15-26)30(39-21-25-12-6-2-7-13-25)29(41-33)23-38-20-24-10-4-1-5-11-24/h1-19,29-31,33H,20-23H2/t29-,30-,31+,33?/m1/s1
• InChIKey: VBDBDZHLJKDSSB-UFRUDBOASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]oxolan-2-yl 4-nitrobenzoate
• IUPAC Traditional name: (3S,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]oxolan-2-yl 4-nitrobenzoate
• Synonyms: 2,3,5-Tri-O-benzyl-1-O-(4-nitrobenzoyl)-D-arabinofuranose, predominantly α anomer; 1-O-(4-Nitrobenzoyl)-2,3,5-tri-O-benzyl-D-arabinofuranose; 2,3,5-Tri-O-benzyl-1-O-(4-nitrobenzoyl)-D-arabinofuranose; 2,3,5-Tri-O-benzyl-D-arabinofuranose 1-(4-nitrobenzoate); 2,3,5-三-O-苄基-1-O-(4-硝基苯甲酰基)-D-阿拉伯呋喃糖（主要为 α 异头物）; 1-O-(4-硝基苯甲酰基)-2,3,5-三-O-苄基-D-阿拉伯呋喃糖; 2,3,5-三-O-苄基-1-O-(4-硝基苯甲酰基)-D-阿拉伯呋喃糖; 2,3,5-三-O-苄基-D-阿拉伯呋喃糖-1-(4-硝基苯甲酸酯)

Database IDs

• CAS Number: 52522-49-3; 31598-79-5
• EC Number: 257-992-5
• MDL Number: MFCD00038477
• Beilstein Number: 1303859
• PubChem SID: 24862368; 162233075; 24859889
• PubChem CID: 97076

CALCULATED PROPERTIES

• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 7.2358785
• LogD (pH = 7.4): 7.2358785
• Log P: 7.2358785
• Molar Refractivity: 155.199 cm^3
• Polarizability: 60.31644 Å^3
• Polar Surface Area: 109.04 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 69-72 °C(lit.); 86-88 °C(lit.)
• Optical Rotation: [α]20/D +57°, c = 1.2 in methylene chloride

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C33H31NO8

DETAILS

Sigma Aldrich - 332356

Packaging
5 g in glass bottle