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

Base Information

Chemical Name: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
CAS No.:851346-10-6
Molecular Formula:C₄₃H₄₈N₂O₈SSi
Molecular Weight:781.014
Hs Code.:

thiocarbonic acid <i>O</i>-[4-benzyloxy-5-(<i>tert</i>-butyl-diphenyl-silanyloxymethyl)-5-ethoxymethyl-2-(5-methyl-2,4-dioxo-3,4-dihydro-2<i>H</i>-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester <i>O</i>-phenyl ester

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 6 articles about 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 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%

: 851346-00-4
1-[4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-ethoxymethyl-3-hydroxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

: 1005-56-7
phenylcarbonochloridothioate

: 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

Guidance literature:: With dmap; In acetonitrile; at 20 ℃; for 1h;
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

: 851346-10-6
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

Guidance literature:: Multi-step reaction with 4 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

With pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sodium methylate; In methanol; acetonitrile; 2: Vorbrueggen glycosylation;
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

: 851346-10-6
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

Guidance literature:: Multi-step reaction with 5 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

With pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sodium methylate; acetic acid; trifluoroacetic acid; In methanol; acetonitrile; 3: Vorbrueggen glycosylation;
DOI:10.1002/chem.200401114