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

Base Information

Chemical Name:1-[4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-ethoxymethyl-3-hydroxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
CAS No.:851346-00-4
Molecular Formula:C₃₆H₄₄N₂O₇Si
Molecular Weight:644.84
Hs Code.:

1-[4-benzyloxy-5-(<i>tert</i>-butyl-diphenyl-silanyloxymethyl)-5-ethoxymethyl-3-hydroxy-tetrahydro-furan-2-yl]-5-methyl-1<i>H</i>-pyrimidine-2,4-dione

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

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

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

There total 5 articles about 1-[4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-ethoxymethyl-3-hydroxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 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: 94.0%

: 851345-99-8
1-(2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-ethoxymethylene-β-D-ribo-pentofuranosyl)thymine

: 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

Guidance literature:: With sodium methylate; In methanol; 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

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

Guidance literature:: Multi-step reaction with 3 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

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

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

Guidance literature:: Multi-step reaction with 4 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

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