1-(5-(N-(phenoxyacetyl)amino)-N-(4,4'-dimethoxytrityl)phthalimid-3-yl)-3-O-[(2-cyanoethoxy)diisopropylaminophosphanyl]-5-O-(4,4'-dimethoxytrityl)-1,2-dideoxy-β-D-ribofuranose

Base Information

Chemical Name:1-(5-(N-(phenoxyacetyl)amino)-N-(4,4'-dimethoxytrityl)phthalimid-3-yl)-3-O-[(2-cyanoethoxy)diisopropylaminophosphanyl]-5-O-(4,4'-dimethoxytrityl)-1,2-dideoxy-β-D-ribofuranose
CAS No.:1422958-97-1
Molecular Formula:C₇₂H₇₃N₄O₁₂P
Molecular Weight:1217.36
Hs Code.:

1-(5-(N-(phenoxyacetyl)amino)-N-(4,4'-dimethoxytrityl)phthalimid-3-yl)-3-O-[(2-cyanoethoxy)diisopropylaminophosphanyl]-5-O-(4,4'-dimethoxytrityl)-1,2-dideoxy-β-D-ribofuranose

Synonyms:1-(5-(N-(phenoxyacetyl)amino)-N-(4,4'-dimethoxytrityl)phthalimid-3-yl)-3-O-[(2-cyanoethoxy)diisopropylaminophosphanyl]-5-O-(4,4'-dimethoxytrityl)-1,2-dideoxy-β-D-ribofuranose

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Chemical Property of 1-(5-(N-(phenoxyacetyl)amino)-N-(4,4'-dimethoxytrityl)phthalimid-3-yl)-3-O-[(2-cyanoethoxy)diisopropylaminophosphanyl]-5-O-(4,4'-dimethoxytrityl)-1,2-dideoxy-β-D-ribofuranose

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Technology Process of 1-(5-(N-(phenoxyacetyl)amino)-N-(4,4'-dimethoxytrityl)phthalimid-3-yl)-3-O-[(2-cyanoethoxy)diisopropylaminophosphanyl]-5-O-(4,4'-dimethoxytrityl)-1,2-dideoxy-β-D-ribofuranose

There total 19 articles about 1-(5-(N-(phenoxyacetyl)amino)-N-(4,4'-dimethoxytrityl)phthalimid-3-yl)-3-O-[(2-cyanoethoxy)diisopropylaminophosphanyl]-5-O-(4,4'-dimethoxytrityl)-1,2-dideoxy-β-D-ribofuranose 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: 67.0%

: 1422958-95-9
1-(5-(N-(phenoxyacetyl)amino)-N-(4,4'-dimethoxytrityl)phthalimid-3-yl)-5-O-(4,4'-dimethoxytrityl)-1,2-dideoxy-β-D-ribofuranose

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

: 1422958-97-1
1-(5-(N-(phenoxyacetyl)amino)-N-(4,4'-dimethoxytrityl)phthalimid-3-yl)-3-O-[(2-cyanoethoxy)diisopropylaminophosphanyl]-5-O-(4,4'-dimethoxytrityl)-1,2-dideoxy-β-D-ribofuranose

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 4h; Inert atmosphere;
DOI:10.1021/jo302768f

Reference yield:

: 1975-52-6
5-nitro-o-toluic acid

: 1422958-97-1
1-(5-(N-(phenoxyacetyl)amino)-N-(4,4'-dimethoxytrityl)phthalimid-3-yl)-3-O-[(2-cyanoethoxy)diisopropylaminophosphanyl]-5-O-(4,4'-dimethoxytrityl)-1,2-dideoxy-β-D-ribofuranose

Guidance literature:: Multi-step reaction with 11 steps

1: N-Bromosuccinimide; sulfuric acid / 2.5 h / 60 °C

2: sodium hydroxide; potassium permanganate / water / 60 - 100 °C

3: urea / o-xylene / 4 h / 160 °C

4: tris(pentafluorophenyl)phosphine; triethylamine; palladium diacetate / acetonitrile / 82 °C / Inert atmosphere

5: sodium tris(acetoxy)borohydride / acetonitrile / 1 h / 0 °C / Inert atmosphere

6: pyridine; 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

7: sodium hydrogen sulfide / ethanol; water / 1 h / 78 °C

8: pyridine / 20 °C / Inert atmosphere

9: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 20 °C / Inert atmosphere

10: pyridine; triethylamine / 30 °C / Inert atmosphere

11: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; sodium hydrogen sulfide; potassium permanganate; N-Bromosuccinimide; sulfuric acid; palladium diacetate; sodium tris(acetoxy)borohydride; triethylamine tris(hydrogen fluoride); triethylamine; N-ethyl-N,N-diisopropylamine; urea; tris(pentafluorophenyl)phosphine; sodium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; o-xylene; water; N,N-dimethyl-formamide; acetonitrile; 4: |Heck Reaction;
DOI:10.1021/jo302768f

Reference yield:

: 1422958-85-7
3-iodo-5-nitrophthalimide

: 1422958-97-1
1-(5-(N-(phenoxyacetyl)amino)-N-(4,4'-dimethoxytrityl)phthalimid-3-yl)-3-O-[(2-cyanoethoxy)diisopropylaminophosphanyl]-5-O-(4,4'-dimethoxytrityl)-1,2-dideoxy-β-D-ribofuranose

Guidance literature:: Multi-step reaction with 6 steps

1: sodium hydrogen sulfide / ethanol; water / 1 h / 78 °C

2: pyridine; 1H-imidazole / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

3: tris(pentafluorophenyl)phosphine; triethylamine; palladium diacetate / acetonitrile / 82 °C / Inert atmosphere

4: sodium tris(acetoxy)borohydride; acetic acid / acetonitrile / 1 h / 0 °C / Inert atmosphere

5: pyridine; triethylamine / 30 °C / Inert atmosphere

6: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; sodium hydrogen sulfide; palladium diacetate; sodium tris(acetoxy)borohydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; tris(pentafluorophenyl)phosphine; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile; 3: |Heck Reaction;
DOI:10.1021/jo302768f