2'-O-<(tert-butyl)dimethylsilyl>-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine

Base Information

• Chemical Name: 2'-O-<(tert-butyl)dimethylsilyl>-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine
• CAS No.: 153866-41-2
• Molecular Formula: C₃₅H₄₄N₂O₈SSi
• Molecular Weight: 680.894
• Mol file: 153866-41-2.mol

Synonyms:2'-O-<(tert-butyl)dimethylsilyl>-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine

Chemical Property of 2'-O-<(tert-butyl)dimethylsilyl>-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-O-<(tert-butyl)dimethylsilyl>-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine

There total 1 articles about 2'-O-<(tert-butyl)dimethylsilyl>-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine 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: 96.0%

3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine (101527-65-5) + tert-butyldimethylsilyl chloride (18162-48-6) → 2'-O-<(tert-butyl)dimethylsilyl>-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine (153866-41-2)

Guidance literature:

With 1H-imidazole; In dichloromethane; 1.) 0 deg C, 1 h; 2.) room temp., 24 h;

DOI:10.1002/hlca.19930760715

Reference yield: 21.0%

2'-O-<(tert-butyl)dimethylsilyl>-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine (153866-41-2) → 2',2'''-bis-O-<(tert-butyl)dimethylsilyl>-3',3'''-dideoxy-3',3'''-oxy-5',5'''-bis-O-(triphenylmethyl)bis(2',3'-secouridine) (153866-44-5) + 2'-O-<(tert-butyl)dimethylsilyl>-3'-(2'-O-<(tert-butyl)dimethylsilyl>-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridin-3-yl)-3'-deoxy-5'-O-(triphenylmethyl)-2',3'-secouridine

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 16h; Heating;

DOI:10.1002/hlca.19930760715

Reference yield:

2'-O-<(tert-butyl)dimethylsilyl>-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine (153866-41-2) → 3',3'''-dideoxy-3',3'''-oxy-5',5'''-bis-O-(triphenylmethyl)bis(2',3'-secouridine)

Guidance literature:

Multi-step reaction with 2 steps

1: 31 percent / DBU / acetonitrile / 16 h / Heating

2: 37 percent / Bu₄NF (1N) / tetrahydrofuran / 22 h / Ambient temperature

With tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; acetonitrile;

DOI:10.1002/hlca.19930760715

upstream raw materials:

3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine

tert-butyldimethylsilyl chloride

Downstream raw materials:

2',2'''-bis-O-<(tert-butyl)dimethylsilyl>-3',3'''-dideoxy-3',3'''-oxy-5',5'''-bis-O-(triphenylmethyl)bis(2',3'-secouridine)