(1R,5R,6R,8S)-3-aza-8-(2-cyanoethoxy(diisopropylamino)-phosphinoxy)-1-(4,4'-dimethoxytrityloxymethyl)-3-methyl-6-(thymin-1-yl)-4,7-dioxabicyclo[3.2.1]octan-2-one

Base Information

Chemical Name:(1R,5R,6R,8S)-3-aza-8-(2-cyanoethoxy(diisopropylamino)-phosphinoxy)-1-(4,4'-dimethoxytrityloxymethyl)-3-methyl-6-(thymin-1-yl)-4,7-dioxabicyclo[3.2.1]octan-2-one
CAS No.:1300591-03-0
Molecular Formula:C₄₂H₅₀N₅O₁₀P
Molecular Weight:815.86
Hs Code.:

(1R,5R,6R,8S)-3-aza-8-(2-cyanoethoxy(diisopropylamino)-phosphinoxy)-1-(4,4'-dimethoxytrityloxymethyl)-3-methyl-6-(thymin-1-yl)-4,7-dioxabicyclo[3.2.1]octan-2-one

Synonyms:(1R,5R,6R,8S)-3-aza-8-(2-cyanoethoxy(diisopropylamino)-phosphinoxy)-1-(4,4'-dimethoxytrityloxymethyl)-3-methyl-6-(thymin-1-yl)-4,7-dioxabicyclo[3.2.1]octan-2-one

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Chemical Property of (1R,5R,6R,8S)-3-aza-8-(2-cyanoethoxy(diisopropylamino)-phosphinoxy)-1-(4,4'-dimethoxytrityloxymethyl)-3-methyl-6-(thymin-1-yl)-4,7-dioxabicyclo[3.2.1]octan-2-one

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Technology Process of (1R,5R,6R,8S)-3-aza-8-(2-cyanoethoxy(diisopropylamino)-phosphinoxy)-1-(4,4'-dimethoxytrityloxymethyl)-3-methyl-6-(thymin-1-yl)-4,7-dioxabicyclo[3.2.1]octan-2-one

There total 19 articles about (1R,5R,6R,8S)-3-aza-8-(2-cyanoethoxy(diisopropylamino)-phosphinoxy)-1-(4,4'-dimethoxytrityloxymethyl)-3-methyl-6-(thymin-1-yl)-4,7-dioxabicyclo[3.2.1]octan-2-one 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: 70.0%

: 1300591-01-8
(1R,5R,6R,8S)-3-aza-1-(4,4'-dimethoxytrityloxymethyl)-8-hydroxy-3-methyl-6-(thymin-1-yl)-4,7-dioxabicyclo[3.2.1]octan-2-one

: 102691-36-1
N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite

: 1300591-03-0
(1R,5R,6R,8S)-3-aza-8-(2-cyanoethoxy(diisopropylamino)-phosphinoxy)-1-(4,4'-dimethoxytrityloxymethyl)-3-methyl-6-(thymin-1-yl)-4,7-dioxabicyclo[3.2.1]octan-2-one

Guidance literature:: With 4,5-dicyano-1H-imidazole; In acetonitrile; at 20 ℃; for 7h;
DOI:10.1021/jo201597e

Reference yield:

: 1300590-97-9
(1R,5R,6R,8S)-3-aza-8-benzyloxy-1-benzyloxymethyl-3-methyl-6-(thymin-1-yl)-4,7-dioxabicyclo[3.2.1]octan-2-one

: 1300591-03-0
(1R,5R,6R,8S)-3-aza-8-(2-cyanoethoxy(diisopropylamino)-phosphinoxy)-1-(4,4'-dimethoxytrityloxymethyl)-3-methyl-6-(thymin-1-yl)-4,7-dioxabicyclo[3.2.1]octan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: 20% palladium hydroxide on charcoal; hydrogen / ethanol; chloroform / 20 °C

2: pyridine; triethylamine / 8 h / 20 °C

3: 4,5-dicyano-1H-imidazole / acetonitrile / 7 h / 20 °C

With pyridine; 4,5-dicyano-1H-imidazole; 20% palladium hydroxide on charcoal; hydrogen; triethylamine; In ethanol; chloroform; acetonitrile;
DOI:10.1021/jo201597e

Reference yield:

: 1300590-91-3
2'-O-amino-3',5'-di-O-benzyl-4'-carboxy-5-methyluridine

: 1300591-03-0
(1R,5R,6R,8S)-3-aza-8-(2-cyanoethoxy(diisopropylamino)-phosphinoxy)-1-(4,4'-dimethoxytrityloxymethyl)-3-methyl-6-(thymin-1-yl)-4,7-dioxabicyclo[3.2.1]octan-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: methanol; water / 2 h / 20 °C

2: methanol; pyridinium p-toluenesulfonate; sodium cyanoborohydride / 2.17 h / 0 - 20 °C

3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 20 °C

4: 20% palladium hydroxide on charcoal; hydrogen / ethanol; chloroform / 20 °C

5: pyridine; triethylamine / 8 h / 20 °C

6: 4,5-dicyano-1H-imidazole / acetonitrile / 7 h / 20 °C

With pyridine; methanol; 4,5-dicyano-1H-imidazole; 20% palladium hydroxide on charcoal; hydrogen; pyridinium p-toluenesulfonate; sodium cyanoborohydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In methanol; ethanol; chloroform; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo201597e