5'-O-TBDPS-3'-C-[N-[N-(2-trifluoroacetylaminoethyl)]-6-carbamoylhex-2(Z)-enyl]-3'-deoxythymidine

Base Information

Chemical Name:5'-O-TBDPS-3'-C-[N-[N-(2-trifluoroacetylaminoethyl)]-6-carbamoylhex-2(Z)-enyl]-3'-deoxythymidine
CAS No.:287185-74-4
Molecular Formula:C₃₇H₄₇F₃N₄O₆Si
Molecular Weight:728.884
Hs Code.:

Synonyms:5'-O-TBDPS-3'-C-[N-[N-(2-trifluoroacetylaminoethyl)]-6-carbamoylhex-2(Z)-enyl]-3'-deoxythymidine

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Chemical Property of 5'-O-TBDPS-3'-C-[N-[N-(2-trifluoroacetylaminoethyl)]-6-carbamoylhex-2(Z)-enyl]-3'-deoxythymidine

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Technology Process of 5'-O-TBDPS-3'-C-[N-[N-(2-trifluoroacetylaminoethyl)]-6-carbamoylhex-2(Z)-enyl]-3'-deoxythymidine

There total 3 articles about 5'-O-TBDPS-3'-C-[N-[N-(2-trifluoroacetylaminoethyl)]-6-carbamoylhex-2(Z)-enyl]-3'-deoxythymidine 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: 95.0%

: 407-25-0
trifluoroacetic anhydride

: 287185-73-3
5'-O-TBDPS-3'-C-[N-(2-aminoethyl)-6-carbamoylhex-2(Z)-enyl]-3'-deoxythymidine

: 287185-74-4
5'-O-TBDPS-3'-C-[N-[N-(2-trifluoroacetylaminoethyl)]-6-carbamoylhex-2(Z)-enyl]-3'-deoxythymidine

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1055/s-2000-6388

Reference yield:

: 17814-85-6
(4-carboxybutyl)triphenylphosphonium bromide

: 287185-74-4
5'-O-TBDPS-3'-C-[N-[N-(2-trifluoroacetylaminoethyl)]-6-carbamoylhex-2(Z)-enyl]-3'-deoxythymidine

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaN(TMS)2 / tetrahydrofuran / 0.25 h / 20 °C

1.2: 68 percent / tetrahydrofuran / 0.25 h / 20 °C

2.1: DIPEA / dimethylformamide; dioxane / 0.33 h / 20 °C

3.1: dimethylformamide; dioxane / 0.17 h / 20 °C

4.1: 95 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

With sodium hexamethyldisilazane; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 1.1: Elimination / 1.2: Condensation / 2.1: Substitution / 3.1: Acylation / 4.1: Acylation;
DOI:10.1055/s-2000-6388

Reference yield:

: (Z)-7-[(2S,3S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-hept-5-enoic acid 2,5-dioxo-pyrrolidin-1-yl ester

: 287185-74-4
5'-O-TBDPS-3'-C-[N-[N-(2-trifluoroacetylaminoethyl)]-6-carbamoylhex-2(Z)-enyl]-3'-deoxythymidine

Guidance literature:: Multi-step reaction with 2 steps

1: dimethylformamide; dioxane / 0.17 h / 20 °C

2: 95 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

With triethylamine; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: Acylation;
DOI:10.1055/s-2000-6388