3',5'-bis(O-tert-butyldimethylsilyl)-2'-deoxy-5-(2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosyl)oxymethyluridine

Base Information

Chemical Name:3',5'-bis(O-tert-butyldimethylsilyl)-2'-deoxy-5-(2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosyl)oxymethyluridine
CAS No.:942270-75-9
Molecular Formula:C₅₆H₆₈N₂O₁₅Si₂
Molecular Weight:1065.33
Hs Code.:

Synonyms:3',5'-bis(O-tert-butyldimethylsilyl)-2'-deoxy-5-(2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosyl)oxymethyluridine

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Chemical Property of 3',5'-bis(O-tert-butyldimethylsilyl)-2'-deoxy-5-(2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosyl)oxymethyluridine

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Technology Process of 3',5'-bis(O-tert-butyldimethylsilyl)-2'-deoxy-5-(2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosyl)oxymethyluridine

There total 6 articles about 3',5'-bis(O-tert-butyldimethylsilyl)-2'-deoxy-5-(2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosyl)oxymethyluridine 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: 65.0%

: 183901-63-5
2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate

: 354581-59-2
3',5'-bis(O-tert-butyldimethylsilyl)-5-hydroxymethyl-2'-deoxyuridine

: 942270-75-9
3',5'-bis(O-tert-butyldimethylsilyl)-2'-deoxy-5-(2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosyl)oxymethyluridine

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at -25 ℃; for 1.5h;
DOI:10.1002/anie.200604635

Reference yield:

: 942270-62-4
3',5'-bis(O-tert-butyldimethylsilyl)-5-methoxyacetyloxymethyl-2'-deoxyuridine

: 942270-75-9
3',5'-bis(O-tert-butyldimethylsilyl)-2'-deoxy-5-(2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosyl)oxymethyluridine

Guidance literature:: Multi-step reaction with 2 steps

1: 97 percent / K₂CO₃; methanol / 1 h

2: 65 percent / TMSOTf / 1,2-dichloro-ethane / 1.5 h / -25 °C

With methanol; trimethylsilyl trifluoromethanesulfonate; potassium carbonate; In 1,2-dichloro-ethane; 2: Schmidt condensation reaction;
DOI:10.1002/anie.200604635

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 942270-75-9
3',5'-bis(O-tert-butyldimethylsilyl)-2'-deoxy-5-(2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosyl)oxymethyluridine

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / imidazole / dimethylformamide / 2 h / 50 °C

2: N-bromosuccinimide; azoisobutyronitrile / benzene / 0.67 h / 80 °C

3: 12.5 g / dimethylformamide / 1 h

4: 97 percent / K₂CO₃; methanol / 1 h

5: 65 percent / TMSOTf / 1,2-dichloro-ethane / 1.5 h / -25 °C

With 1H-imidazole; methanol; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; potassium carbonate; In 1,2-dichloro-ethane; N,N-dimethyl-formamide; benzene; 5: Schmidt condensation reaction;
DOI:10.1002/anie.200604635