2',3'-Di-O-(tert-butyldiMethylsilyl)-2'-deoxycytidine

Base Information

• Chemical Name: 2',3'-Di-O-(tert-butyldiMethylsilyl)-2'-deoxycytidine
• CAS No.: 51549-29-2
• Molecular Formula: C₂₁H₄₁N₃O₄Si₂
• Molecular Weight: 455.745
• Mol file: 51549-29-2.mol

Synonyms:2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)cytidine

Chemical Property of 2',3'-Di-O-(tert-butyldiMethylsilyl)-2'-deoxycytidine

Chemical Property:

• Melting Point: 186-188°C
• Storage Temp.: Refrigerator
• Solubility.: Dimethylsulfoxide, Ethylacetate

Purity/Quality:

97% ^*data from raw suppliers

2'',3''-Di-O-(tert-butyldimethylsilyl)-2''-deoxycytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 2'',3''-Di-O-(tert-butyldimethylsilyl)-2''-deoxycytidine is an intermediate for biosynthesis of cholyl-CoA and oligodeoxyribonucleotides. 2',3'-Di-O-(tert-butyldimethylsilyl)-2'-deoxycytidine is an intermediate for biosynthesis of cholyl-CoA and oligodeoxyribonucleotides.

Technology Process of 2',3'-Di-O-(tert-butyldiMethylsilyl)-2'-deoxycytidine

There total 1 articles about 2',3'-Di-O-(tert-butyldiMethylsilyl)-2'-deoxycytidine 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:

methyl-d3-magnesium iodide (41251-37-0) + 5-iodo-3'O,5'O-bis(tert-butyldimethylsilyl)-2'-deoxycytidine (478843-96-8) → 3',5'-O-bis(tert-butyldimethylsilyl)-5-([D3]methyl)-2'-deoxycytidine (1245724-75-7) + 2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)cytidine (51549-29-2)

Guidance literature:

methyl-d3-magnesium iodide; 5-iodo-3'O,5'O-bis(tert-butyldimethylsilyl)-2'-deoxycytidine; In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.0833333h; Inert atmosphere;

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) chloride; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃; for 18h; Inert atmosphere;

DOI:10.1002/anie.202107277

Reference yield: 90.0%

tritylsulfenyl chloride (24165-03-5) + 2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)cytidine (51549-29-2) → 3',5'-O-[bis-(tert-butyldimethylsilyl)]-4-N-(triphenylmethylsulfenyl)deoxycytidine (154738-03-1)

Guidance literature:

With sodium carbonate; In dichloromethane; for 2h; Ambient temperature;

Reference yield: 90.0%

4,4',4''-tris(benzoyloxy)trityl bromide (86610-66-4) + 2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)cytidine (51549-29-2) → C61H67N3O10Si2 (104006-66-8)

Guidance literature:

With 2,6-dimethylpyridine; silver nitrate; In N,N-dimethyl-formamide; for 1h; Ambient temperature;

DOI:10.1016/S0040-4020(01)91344-4

upstream raw materials:

methyl-d3-magnesium iodide

5-iodo-3'O,5'O-bis(tert-butyldimethylsilyl)-2'-deoxycytidine

Downstream raw materials:

3',5'-O-[bis-(tert-butyldimethylsilyl)]-4-N-(triphenylmethylsulfenyl)deoxycytidine

C₆₁H₆₇N₃O₁₀Si₂

1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-4-(2-nitro-phenylsulfanylamino)-1H-pyrimidin-2-one

1-Benzoyl-3-{1-[(2R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-thiourea

Refernces