(2R,3S,5R)-5-(4-ACETAMIDO-2-OXOPYRIMIDIN-1(2H)-YL)-2-((BIS(4-METHOXYPHENYL)(PHENYL)METHOXY)METHYL)TETRAHYDROFURAN-3-YL 2-CYANOETHYL DIISOPROPYLPHOSPHORAMIDITE

Base Information

• Chemical Name: (2R,3S,5R)-5-(4-ACETAMIDO-2-OXOPYRIMIDIN-1(2H)-YL)-2-((BIS(4-METHOXYPHENYL)(PHENYL)METHOXY)METHYL)TETRAHYDROFURAN-3-YL 2-CYANOETHYL DIISOPROPYLPHOSPHORAMIDITE
• CAS No.: 154110-40-4
• Molecular Formula: C₄₁H₅₀N₅O₈P
• Molecular Weight: 771.85
• Hs Code.: 2934999090
• Mol file: 154110-40-4.mol

Synonyms:dC Ac phosphoramidite;(2R,3S,5R)-5-(4-ACETAMIDO-2-OXOPYRIMIDIN-1(2H)-YL)-2-((BIS(4-METHOXYPHENYL)(PHENYL)METHOXY)METHYL)TETRAHYDROFURAN-3-YL 2-CYANOETHYL DIISOPROPYLPHOSPHORAMIDITE;

Chemical Property of (2R,3S,5R)-5-(4-ACETAMIDO-2-OXOPYRIMIDIN-1(2H)-YL)-2-((BIS(4-METHOXYPHENYL)(PHENYL)METHOXY)METHYL)TETRAHYDROFURAN-3-YL 2-CYANOETHYL DIISOPROPYLPHOSPHORAMIDITE

Chemical Property:

• PKA: 10.26±0.20(Predicted)
• PSA: 159.99000
• LogP: 7.24928
• Storage Temp.: ?20°C

Purity/Quality:

99% ^*data from raw suppliers

Ac-dCPhosphoramidite ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Ac-dC phosphoramidite is a nucleoside used in the preparation of cytidine-?based nucleotide-?lipids which can act as supramolecular gelators depending on both the nucleobase and the presence of salts.

Technology Process of (2R,3S,5R)-5-(4-ACETAMIDO-2-OXOPYRIMIDIN-1(2H)-YL)-2-((BIS(4-METHOXYPHENYL)(PHENYL)METHOXY)METHYL)TETRAHYDROFURAN-3-YL 2-CYANOETHYL DIISOPROPYLPHOSPHORAMIDITE

There total 4 articles about (2R,3S,5R)-5-(4-ACETAMIDO-2-OXOPYRIMIDIN-1(2H)-YL)-2-((BIS(4-METHOXYPHENYL)(PHENYL)METHOXY)METHYL)TETRAHYDROFURAN-3-YL 2-CYANOETHYL DIISOPROPYLPHOSPHORAMIDITE 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: 85.0%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + 5’-O-(4,4’dimethoxytrityl)-N4-(acetyl)-2'-deoxycytidine (100898-63-3) → 5'-O-(4,4'-dimethoxytrityl)-N-acetyl-2'-deoxycytidine 3'-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite (157543-67-4,157543-68-5,154110-40-4)

Guidance literature:

DOI:10.1016/S0040-4039(00)73341-7

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → 5'-O-(4,4'-dimethoxytrityl)-N-acetyl-2'-deoxycytidine 3'-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite (157543-67-4,157543-68-5,154110-40-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / pyridine

2: 85 percent / iPr₂NEt / tetrahydrofuran

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

DOI:10.1080/07328319708006236

Reference yield:

N4-acetyl-2'-deoxycytidine (32909-05-0) → 5'-O-(4,4'-dimethoxytrityl)-N-acetyl-2'-deoxycytidine 3'-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite (157543-67-4,157543-68-5,154110-40-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / pyridine

2: 85 percent / iPr₂NEt / tetrahydrofuran

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

DOI:10.1080/07328319708006236

upstream raw materials:

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

5’-O-(4,4’dimethoxytrityl)-N4-(acetyl)-2'-deoxycytidine

4,4'-dimethoxytrityl chloride

N⁴-acetyl-2'-deoxycytidine

Downstream raw materials:

(2R,3S,5R)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-2-(hydroxymethyl)tetrahydrofuran-3-yl((2R,3S,4R,5R)-4-azido-5-(6-benzamido-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl)methyl 2-cyanoethyl phosphate

Refernces

• 1、 Reddy, M. P.,Hanna, N. B.,Farooqui, Firdous. "Fast Cleavage and Deprotection of Oligonucleotides". . p. 4311 - 4314. Retrieved 2007/10/02.