2'-O-T-BUTYLDIMETHYLSILYL-3'-O-[(DIISOPROPYLAMINO)(2-CYANOETHOXY)PHOSPHINO]-5'-O-(4,4'-DIMETHOXYTRITYL)-2(1H)-PYRIMIDINONE-1-BETA-D-RIBOSIDE

Base Information

• Chemical Name: 2'-O-T-BUTYLDIMETHYLSILYL-3'-O-[(DIISOPROPYLAMINO)(2-CYANOETHOXY)PHOSPHINO]-5'-O-(4,4'-DIMETHOXYTRITYL)-2(1H)-PYRIMIDINONE-1-BETA-D-RIBOSIDE
• CAS No.: 155831-90-6
• Molecular Formula: C₄₅H₆₁N₄O₈PSi
• Molecular Weight: 845.061
• Mol file: 155831-90-6.mol

Synonyms:2’-O-T-BUTYLDIMETHYLSILYL-3’-O-[(DIISOPROPYLAMINO)(2-CYANOETHOXY)PHOSPHINO]-5’-O-(4,4’-DIMETHOXYTRITYL)-2(1H)-PYRIMIDINONE-1-BETA-D-RIBOSIDE;4HC CEP;ZEBULARINE CEP

Chemical Property of 2'-O-T-BUTYLDIMETHYLSILYL-3'-O-[(DIISOPROPYLAMINO)(2-CYANOETHOXY)PHOSPHINO]-5'-O-(4,4'-DIMETHOXYTRITYL)-2(1H)-PYRIMIDINONE-1-BETA-D-RIBOSIDE

Chemical Property:

• PSA: 140.12000
• LogP: 9.21818

Purity/Quality:

97% ^*data from raw suppliers

ZebularineCEP ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Zebularine CEP (CAS# 155831-90-6) is a fluorescent nucleotide, and has been incorporated into oligoribonucleotides to form a useful probe for the exocyclic amino function in cytidine.

Technology Process of 2'-O-T-BUTYLDIMETHYLSILYL-3'-O-[(DIISOPROPYLAMINO)(2-CYANOETHOXY)PHOSPHINO]-5'-O-(4,4'-DIMETHOXYTRITYL)-2(1H)-PYRIMIDINONE-1-BETA-D-RIBOSIDE

There total 6 articles about 2'-O-T-BUTYLDIMETHYLSILYL-3'-O-[(DIISOPROPYLAMINO)(2-CYANOETHOXY)PHOSPHINO]-5'-O-(4,4'-DIMETHOXYTRITYL)-2(1H)-PYRIMIDINONE-1-BETA-D-RIBOSIDE 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: 40.0%

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1) + 2-pyrimidinone-1-β-D-(2'-O-t-butyldimethylsilyl-5'-O-dimethoxytritylriboside) (170660-44-3) → Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-(2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester (155831-90-6)

Guidance literature:

With 1H-tetrazole; diisopropylamine; In acetonitrile; for 16h; Ambient temperature;

DOI:10.1021/ja971020c

Reference yield:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) → Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-(2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester (155831-90-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 74 percent / hexamethyldisilazane, TMS-Cl, SnCl₄ / acetonitrile

2: 87 percent / ammonia / methanol / 15 h / 0 °C

3: pyridine

4: pyridine

5: DMAP, iPr₂NEt / CH₂Cl₂

With pyridine; dmap; chloro-trimethyl-silane; ammonia; tin(IV) chloride; N-ethyl-N,N-diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In methanol; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(00)76768-2

Reference yield:

2-pyrimidinone-1-β-D-(5'-O-dimethoxytritylriboside) (170660-47-6) → Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-(2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester (155831-90-6)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine

2: DMAP, iPr₂NEt / CH₂Cl₂

With pyridine; dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1016/S0040-4039(00)76768-2

upstream raw materials:

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

2-pyrimidinone-1-β-D-(2'-O-t-butyldimethylsilyl-5'-O-dimethoxytritylriboside)

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Refernces

• 1、 Adams, Chris J.,Murray, James B.,Arnold, John R.P.,Stockley, Peter G.. "Incorporation of a fluorescent nucleotide into oligoribonucleotides". . p. 1597 - 1600. Retrieved 2007/10/02.