N-Acetyl-5'-O-(4,4-dimethoxytrityl)-2'-O-methylcytidine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

Base Information

• Chemical Name: N-Acetyl-5'-O-(4,4-dimethoxytrityl)-2'-O-methylcytidine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite
• CAS No.: 199593-09-4
• Molecular Formula: C₄₂H₅₂N₅O₉P
• Molecular Weight: 801.877
• Hs Code.: 29349990
• Mol file: 199593-09-4.mol

Synonyms:5'-O-DMT-2'-O-Me-rC(N-Ac)-3'-CEDPA

Chemical Property of N-Acetyl-5'-O-(4,4-dimethoxytrityl)-2'-O-methylcytidine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

Chemical Property:

• Melting Point: 102 - 104°C
• PKA: 10.18±0.20(Predicted)
• PSA: 169.22000
• LogP: 6.87418
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

2''-OMe-Ac-CPhosphoramidite(~90%) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2''-OMe-Ac-C Phosphoramidite (CAS# 199593-09-4) is a nucleotide used in the solid-phase synthesis of phosphorothioate oligonucleotides using sulfurization byproducts for in situ capping.

Technology Process of N-Acetyl-5'-O-(4,4-dimethoxytrityl)-2'-O-methylcytidine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

There total 6 articles about N-Acetyl-5'-O-(4,4-dimethoxytrityl)-2'-O-methylcytidine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite 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: 65.0%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + N-(1-((2R,3R,4R,5R)-5-((bis(4-Methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxy-3-methoxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide (199593-08-3) → Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester (199593-09-4,213020-84-9,213020-85-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;

DOI:10.1080/07328319708006236

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester (199593-09-4,213020-84-9,213020-85-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / pyridine

2: 65 percent / iPr₂NEt / tetrahydrofuran

With pyridine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;

DOI:10.1080/07328319708006236

Reference yield:

N4-acetyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)cytidine (85335-73-5) → Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester (199593-09-4,213020-84-9,213020-85-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 70 percent / Ag₂O / benzene / Ambient temperature

2: 60 percent / Bu₄NF / tetrahydrofuran

3: 70 percent / pyridine

4: 65 percent / iPr₂NEt / tetrahydrofuran

With pyridine; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; silver(l) oxide; In tetrahydrofuran; benzene;

DOI:10.1080/07328319708006236

upstream raw materials:

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

N-(1-((2R,3R,4R,5R)-5-((bis(4-Methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxy-3-methoxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide

4,4'-dimethoxytrityl chloride

N₄-acetyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)cytidine

Downstream raw materials:

5'-O-dimethoxytritil-2'-O-methylcytidine-3'-O-(2-cianoethyl-N,N-diisopropylphosphoramidite)

Refernces