2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-oxymethyluridine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

Base Information

Chemical Name:2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-oxymethyluridine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite
CAS No.:629642-46-2
Molecular Formula:C₅₄H₆₇N₄O₁₈P
Molecular Weight:1091.12
Hs Code.:

2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-oxymethyluridine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

Synonyms:2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-oxymethyluridine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

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Chemical Property of 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-oxymethyluridine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

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Technology Process of 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-oxymethyluridine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

There total 13 articles about 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-oxymethyluridine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite 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: 96.0%

: 124482-92-4,89992-70-1
2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

: 629642-44-0
2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxymethyluridine

: 629642-46-2
2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-oxymethyluridine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1002/ejoc.200300218

Reference yield:

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

: 629642-46-2
2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-oxymethyluridine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

Guidance literature:: Multi-step reaction with 7 steps

1: 97 percent / K₂CO₃; methanol / 1 h

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

3: NaOMe; methanol / 12 h

4: pyridine / 6 h / 20 °C

5: Et₃N*3HF; pyridine / tetrahydrofuran / 16 h / 20 °C

6: pyridine / 4 h / 20 °C

7: Et₃N / CH₂Cl₂ / 0.5 h

With pyridine; methanol; trimethylsilyl trifluoromethanesulfonate; sodium methylate; potassium carbonate; triethylamine tris(hydrogen fluoride); triethylamine; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; 2: Schmidt condensation reaction;
DOI:10.1002/anie.200604635

Reference yield:

: 40615-36-9
4,4'-dimethoxytrityl chloride

: 629642-46-2
2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-oxymethyluridine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

Guidance literature:: Multi-step reaction with 2 steps

1: pyridine / 4 h / 20 °C

2: Et₃N / CH₂Cl₂ / 0.5 h

With pyridine; triethylamine; In dichloromethane;
DOI:10.1002/anie.200604635