5'-O-(4,4'-Dimethoxytrityl)-N⁴-isobutyryl-2'-deoxycytidine-3'-(N,N-diisopropyl)methylphosphonamidite

Base Information

• Chemical Name: 5'-O-(4,4'-Dimethoxytrityl)-N⁴-isobutyryl-2'-deoxycytidine-3'-(N,N-diisopropyl)methylphosphonamidite
• CAS No.: 128192-22-3
• Molecular Formula: C₄₁H₅₃N₄O₇P
• Molecular Weight: 744.868

Synonyms:5'-O-(4,4'-Dimethoxytrityl)-N⁴-isobutyryl-2'-deoxycytidine-3'-(N,N-diisopropyl)methylphosphonamidite

Chemical Property of 5'-O-(4,4'-Dimethoxytrityl)-N⁴-isobutyryl-2'-deoxycytidine-3'-(N,N-diisopropyl)methylphosphonamidite

Chemical Property:

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Technology Process of 5'-O-(4,4'-Dimethoxytrityl)-N⁴-isobutyryl-2'-deoxycytidine-3'-(N,N-diisopropyl)methylphosphonamidite

There total 2 articles about 5'-O-(4,4'-Dimethoxytrityl)-N⁴-isobutyryl-2'-deoxycytidine-3'-(N,N-diisopropyl)methylphosphonamidite 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: 78.0%

N,N,N',N'-Tetraisopropyl-P-methylphosphonous diamide (110838-39-6) + N-(1-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)isobutyramide (100898-62-2) → 5'-O-(4,4'-Dimethoxytrityl)-N4-isobutyryl-2'-deoxycytidine-3'-(N,N-diisopropyl)methylphosphonamidite (128192-22-3)

Guidance literature:

With 2,4,6-collidine hydrochloride; In dichloromethane; at 20 ℃;

DOI:10.1002/recl.19941130106

Reference yield:

bis(diisopropylamino)chlorophosphine (56183-63-2) → 5'-O-(4,4'-Dimethoxytrityl)-N4-isobutyryl-2'-deoxycytidine-3'-(N,N-diisopropyl)methylphosphonamidite (128192-22-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / diethyl ether / 1.) 30 min, 2.) 20 deg C, 1 h

2: 78 percent / sym-collidine hydrochloride / CH₂Cl₂ / 20 °C

With 2,4,6-collidine hydrochloride; In diethyl ether; dichloromethane;

DOI:10.1002/recl.19941130106

Reference yield:

5'-O-(4,4'-Dimethoxytrityl)-N4-isobutyryl-2'-deoxycytidine-3'-(N,N-diisopropyl)methylphosphonamidite (128192-22-3) → C48H57N6O13P

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) tetrazole, 2.) I₂, pyridine / 2.) THF, H₂O

2: 1.) 3-ethyl-3-pentanoxymagnesium chloride, 2.) TBAF / 1.) THF, 50 deg C, 4 h, 2.) THF, room temperature, 2 h

With pyridine; 1H-tetrazole; 3-ethyl-3-pentanoxymagnesium chloride; tetrabutyl ammonium fluoride; iodine;

DOI:10.1080/07328319708001359

upstream raw materials:

N,N,N',N'-Tetraisopropyl-P-methylphosphonous diamide

N-(1-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)isobutyramide

bis(diisopropylamino)chlorophosphine

Downstream raw materials:

(R)-Methyl-phosphonic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(4-isobutyrylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2,2,2-trifluoro-1-trifluoromethyl-ethyl ester

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