1-(3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-ethoxymethylene-β-D-ribo-pentofuranosyl)thymine

Base Information

Chemical Name:1-(3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-ethoxymethylene-β-D-ribo-pentofuranosyl)thymine
CAS No.:851346-01-5
Molecular Formula:C₃₆H₄₄N₂O₆Si
Molecular Weight:628.841
Hs Code.:

Synonyms:1-(3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-ethoxymethylene-β-D-ribo-pentofuranosyl)thymine

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Chemical Property of 1-(3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-ethoxymethylene-β-D-ribo-pentofuranosyl)thymine

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Technology Process of 1-(3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-ethoxymethylene-β-D-ribo-pentofuranosyl)thymine

There total 7 articles about 1-(3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-ethoxymethylene-β-D-ribo-pentofuranosyl)thymine 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: 69.0%

: 851346-10-6
thiocarbonic acid O-[4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-ethoxymethyl-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester O-phenyl ester

: 851346-01-5
1-(3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-ethoxymethylene-β-D-ribo-pentofuranosyl)thymine

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 3h; Heating;
DOI:10.1002/chem.200401114

Reference yield:

: 851345-97-6
3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-ethoxymethylene-1,2-isopropylidene-β-D-ribo-pentofuranose

: 851346-01-5
1-(3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-ethoxymethylene-β-D-ribo-pentofuranosyl)thymine

Guidance literature:: Multi-step reaction with 6 steps

1: aq. AcOH; CF₃COOH / 4 h / 20 °C

2: 150.8 mg / DMAP; pyridine / 18 h / 20 °C

3: 91 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / acetonitrile / 1 h / Heating

4: 94 percent / NaOMe / methanol / 1 h / 20 °C

5: 85 percent / DMAP / acetonitrile / 1 h / 20 °C

6: 69 percent / n-Bu₃SnH; AIBN / toluene / 3 h / Heating

With pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tri-n-butyl-tin hydride; sodium methylate; acetic acid; trifluoroacetic acid; In methanol; toluene; acetonitrile; 3: Vorbrueggen glycosylation;
DOI:10.1002/chem.200401114

Reference yield:

: (2S,3R,4S,5R)-4-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-ethoxymethyl-tetrahydro-furan-2,3-diol

: 851346-01-5
1-(3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-ethoxymethylene-β-D-ribo-pentofuranosyl)thymine

Guidance literature:: Multi-step reaction with 5 steps

1: 150.8 mg / DMAP; pyridine / 18 h / 20 °C

2: 91 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / acetonitrile / 1 h / Heating

3: 94 percent / NaOMe / methanol / 1 h / 20 °C

4: 85 percent / DMAP / acetonitrile / 1 h / 20 °C

5: 69 percent / n-Bu₃SnH; AIBN / toluene / 3 h / Heating

With pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tri-n-butyl-tin hydride; sodium methylate; In methanol; toluene; acetonitrile; 2: Vorbrueggen glycosylation;
DOI:10.1002/chem.200401114