(2’R)-3’-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5’-O-(4,4’-dimethoxytrityl)-2’,4’-(N-methyl-2-oxoiminoethano)thymidine

Base Information

Chemical Name:(2’R)-3’-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5’-O-(4,4’-dimethoxytrityl)-2’,4’-(N-methyl-2-oxoiminoethano)thymidine
CAS No.:1300590-71-9
Molecular Formula:C₄₃H₅₂N₅O₉P
Molecular Weight:813.888
Hs Code.:

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

Suppliers and Price of (2’R)-3’-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5’-O-(4,4’-dimethoxytrityl)-2’,4’-(N-methyl-2-oxoiminoethano)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’-(N-methyl-2-oxoiminoethano)thymidine

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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

There total 21 articles about (2’R)-3’-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5’-O-(4,4’-dimethoxytrityl)-2’,4’-(N-methyl-2-oxoiminoethano)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%

: 1300590-69-5
(2’R)-5’-O-(4,4’-dimethoxytrityl)-2’,4’-(N-methyl-2-oxoiminoethano)thymidine

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

: 1300590-71-9
(2’R)-3’-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5’-O-(4,4’-dimethoxytrityl)-2’,4’-(N-methyl-2-oxoiminoethano)thymidine

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere;
DOI:10.1016/j.bmc.2013.04.049

Reference yield: 45.0%

: 1300590-69-5
(2’R)-5’-O-(4,4’-dimethoxytrityl)-2’,4’-(N-methyl-2-oxoiminoethano)thymidine

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

: 1300590-71-9
(2’R)-3’-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5’-O-(4,4’-dimethoxytrityl)-2’,4’-(N-methyl-2-oxoiminoethano)thymidine

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 6h;

Reference yield:

: 233266-76-7
(3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde

: 1300590-71-9
(2’R)-3’-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5’-O-(4,4’-dimethoxytrityl)-2’,4’-(N-methyl-2-oxoiminoethano)thymidine

Guidance literature:: Multi-step reaction with 18 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

1.2: 12 h / 20 °C

2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 19 h / 20 °C / Inert atmosphere

2.2: 0.5 h / 20 °C

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

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

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

5.2: 3.5 h / 0 °C / Reflux; Inert atmosphere

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

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

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

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

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

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

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

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

14.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

15.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

15.2: 2 h / 0 °C

16.1: hydrogen / 10 wt% Pd(OH)2 on carbon / cyclohexane; ethanol / 2 h / Reflux

17.1: pyridine / 17 h / 0 - 20 °C

18.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 0 - 20 °C

With pyridine; dmap; dipyridinium dichromate; n-butyllithium; sodium azide; N,O-bis-(trimethylsilyl)-acetamide; tributylphosphine; trifluoromethane sulfonyl chloride; sulfuric acid; tetrabutyl ammonium fluoride; water; hydrogen; acetic anhydride; sodium hydride; potassium carbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; sodium hydroxide; 10 wt% Pd(OH)2 on carbon; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; toluene; acetonitrile;