Uridine, 5'-((((2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl)oxy)carbonyl)sulfamate)

Base Information

• Chemical Name: Uridine, 5'-((((2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl)oxy)carbonyl)sulfamate)
• CAS No.: 93426-60-9
• Molecular Formula: C₄₄H₃₉N₃O₁₉S
• Molecular Weight: 945.868
• DSSTox Substance ID: DTXSID90239423
• Wikidata: Q83121780
• Mol file: 93426-60-9.mol

Synonyms:5'-O-((((2'',3'',4'',6''-tetra-O-benzoylglucopyranosyl)oxy)carbonyl)amino)sulfonyluridine;P 536;P-536;Uridine, 5'-((((2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl)oxy)carbonyl)sulfamate)

Chemical Property of Uridine, 5'-((((2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl)oxy)carbonyl)sulfamate)

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.59g/cm³
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 19
• Rotatable Bond Count: 20
• Exact Mass: 945.18984720
• Heavy Atom Count: 67
• Complexity: 1920

Purity/Quality:

P 536 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)OCC2C(C(C(C(O2)OC(=O)NS(=O)(=O)OCC3C(C(C(O3)N4C=CC(=O)NC4=O)O)O)OC(=O)C5=CC=CC=C5)OC(=O)C6=CC=CC=C6)OC(=O)C7=CC=CC=C7
• Isomeric SMILES: C1=CC=C(C=C1)C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](O2)OC(=O)NS(=O)(=O)OC[C@@H]3[C@H]([C@H]([C@@H](O3)N4C=CC(=O)NC4=O)O)O)OC(=O)C5=CC=CC=C5)OC(=O)C6=CC=CC=C6)OC(=O)C7=CC=CC=C7

Technology Process of Uridine, 5'-((((2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl)oxy)carbonyl)sulfamate)

There total 6 articles about Uridine, 5'-((((2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl)oxy)carbonyl)sulfamate) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

5'-O-<<<<(2'',3'',4'',6''-tetra-O-benzoyl-α-D-mannopyranosyl)oxy>carbonyl>amino>sulfonyl>-2',3'-O-isopropylideneuridine (113567-37-6) → 5'-O-<<<<(2'',3'',4'',6''-tetra-O-benzoyl-α-D-mannopyranosyl)oxy>carbonyl>amino>sulfonyl>uridine (113567-42-3,93426-60-9)

Guidance literature:

With water; trifluoroacetic acid; for 0.5h; Ambient temperature;

DOI:10.1016/0223-5234(87)90174-7

Reference yield: 55.0%

5'-O-<<<<(2'',3'',4'',6''-tetra-O-benzoyl-α-D-glucopyranosyl)oxy>carbonyl>amino>sulfonyl>-2',3'-O-isopropylideneuridine → 5'-O-<<<<(2'',3'',4'',6''-tetra-O-benzoyl-α-D-glucopyranosyl)oxy>carbonyl>amino>sulfonyl>uridine (93426-60-9)

Guidance literature:

With trifluoroacetic acid; for 1h; Ambient temperature;

DOI:10.1021/jm00379a010

Reference yield:

2,3,4,6-tetra-O-benzoyl-α-D-glucopyranose (66530-18-5) → 5'-O-<<<<(2'',3'',4'',6''-tetra-O-benzoyl-α-D-glucopyranosyl)oxy>carbonyl>amino>sulfonyl>uridine (93426-60-9)

Guidance literature:

Multi-step reaction with 3 steps

1: acetonitrile / -20 - -15 °C

2: pyridine / acetonitrile / 20 h / Ambient temperature

3: 55 percent / aq.TFA / 1 h / Ambient temperature

With pyridine; trifluoroacetic acid; In acetonitrile;

DOI:10.1021/jm00379a010

upstream raw materials:

5'-O-<<<<(2'',3'',4'',6''-tetra-O-benzoyl-α-D-mannopyranosyl)oxy>carbonyl>amino>sulfonyl>-2',3'-O-isopropylideneuridine

2',3'-O-isopropylideneuridine

2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside

2,3,4,6-tetra-O-benzoyl-α-D-glucopyranose