(2’R)-3’-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5’-O-(4,4’-dimethoxytrityl)-2’,4’-(2-oxo-iminoethano)thymidine

Base Information

Chemical Name:(2’R)-3’-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5’-O-(4,4’-dimethoxytrityl)-2’,4’-(2-oxo-iminoethano)thymidine
CAS No.:1300590-61-7
Molecular Formula:C₄₂H₅₀N₅O₉P
Molecular Weight:799.861
Hs Code.:

Synonyms:(2’R)-3’-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5’-O-(4,4’-dimethoxytrityl)-2’,4’-(2-oxo-iminoethano)thymidine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2’R)-3’-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5’-O-(4,4’-dimethoxytrityl)-2’,4’-(2-oxo-iminoethano)thymidine

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Technology Process of (2’R)-3’-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5’-O-(4,4’-dimethoxytrityl)-2’,4’-(2-oxo-iminoethano)thymidine

There total 19 articles about (2’R)-3’-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5’-O-(4,4’-dimethoxytrityl)-2’,4’-(2-oxo-iminoethano)thymidine 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: 73.0%

: 1300590-59-3
(2’R)-5’-O-(4,4’-dimethoxytrityl)-2’,4’-(2-oxoiminoethano)thymidine

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

: 1300590-61-7
(2’R)-3’-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5’-O-(4,4’-dimethoxytrityl)-2’,4’-(2-oxo-iminoethano)thymidine

Guidance literature:: With 1H-tetrazole; In tetrahydrofuran; acetonitrile; at 0 - 20 ℃; for 12h; Inert atmosphere;
DOI:10.1016/j.bmc.2013.04.049

Reference yield: 42.0%

: 1300590-59-3
(2’R)-5’-O-(4,4’-dimethoxytrityl)-2’,4’-(2-oxoiminoethano)thymidine

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

: 1300590-61-7
(2’R)-3’-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5’-O-(4,4’-dimethoxytrityl)-2’,4’-(2-oxo-iminoethano)thymidine

Guidance literature:: With 1H-tetrazole; In tetrahydrofuran; acetonitrile; at 20 ℃; for 2h; Inert atmosphere;

Reference yield:

: 287737-62-6
2-((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethanol

: 1300590-61-7
(2’R)-3’-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5’-O-(4,4’-dimethoxytrityl)-2’,4’-(2-oxo-iminoethano)thymidine

Guidance literature:: Multi-step reaction with 14 steps

1.1: dmap; triethylamine / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

2.1: acetic anhydride; sulfuric acid; acetic acid / 2 h / 20 °C / Inert atmosphere

3.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 1.5 h / Inert atmosphere; Reflux

3.2: 3.5 h / 0 °C / Reflux; Inert atmosphere

4.1: potassium carbonate / methanol / 1 h / 20 °C

5.1: triethylamine; trifluoromethane sulfonyl chloride / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

6.1: sodium hydroxide; water / ethanol / 12 h / 20 °C

7.1: pyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

8.1: sodium azide / N,N-dimethyl-formamide / 13 h / 20 °C / Inert atmosphere

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 17 h / 20 °C / Inert atmosphere

10.1: dipyridinium dichromate / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere; Molecular sieve

11.1: tributylphosphine / toluene; water; tetrahydrofuran / 24 h / 20 °C

12.1: hydrogen / 10 wt% Pd(OH)2 on carbon / tetrahydrofuran / 26 h / 20 °C / Inert atmosphere

12.2: 24 h

13.1: pyridine / 3 h / 0 - 20 °C / Inert atmosphere

14.1: 1H-tetrazole / acetonitrile; tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

With pyridine; 1H-tetrazole; dmap; dipyridinium dichromate; sodium azide; N,O-bis-(trimethylsilyl)-acetamide; tributylphosphine; trifluoromethane sulfonyl chloride; sulfuric acid; tetrabutyl ammonium fluoride; water; hydrogen; acetic anhydride; potassium carbonate; acetic acid; triethylamine; sodium hydroxide; 10 wt% Pd(OH)2 on carbon; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;