6-{[(tert-butyl)diphenylsilyloxy]methyl}-1-[5,6,7-trideoxy-2,3-O-isopropylidene-β-D-ribo-hept-6-ynofuranosyl]uracil

Base Information

Chemical Name:6-{[(tert-butyl)diphenylsilyloxy]methyl}-1-[5,6,7-trideoxy-2,3-O-isopropylidene-β-D-ribo-hept-6-ynofuranosyl]uracil
CAS No.:928034-58-6
Molecular Formula:C₃₁H₃₆N₂O₆Si
Molecular Weight:560.722
Hs Code.:

Synonyms:6-{[(tert-butyl)diphenylsilyloxy]methyl}-1-[5,6,7-trideoxy-2,3-O-isopropylidene-β-D-ribo-hept-6-ynofuranosyl]uracil

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Chemical Property of 6-{[(tert-butyl)diphenylsilyloxy]methyl}-1-[5,6,7-trideoxy-2,3-O-isopropylidene-β-D-ribo-hept-6-ynofuranosyl]uracil

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Technology Process of 6-{[(tert-butyl)diphenylsilyloxy]methyl}-1-[5,6,7-trideoxy-2,3-O-isopropylidene-β-D-ribo-hept-6-ynofuranosyl]uracil

There total 10 articles about 6-{[(tert-butyl)diphenylsilyloxy]methyl}-1-[5,6,7-trideoxy-2,3-O-isopropylidene-β-D-ribo-hept-6-ynofuranosyl]uracil 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:

: 1-(2,2-dimethyl-6-prop-2-ynyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-6-hydroxymethyl-1H-pyrimidine-2,4-dione

: 58479-61-1
tert-butylchlorodiphenylsilane

: 928034-58-6
6-{[(tert-butyl)diphenylsilyloxy]methyl}-1-[5,6,7-trideoxy-2,3-O-isopropylidene-β-D-ribo-hept-6-ynofuranosyl]uracil

Guidance literature:: With 1H-imidazole; dmap; In dichloromethane; at 25 ℃; for 12h;
DOI:10.1002/hlca.200690259

Reference yield:

: 928034-57-5
6-{[(tert-butyl)diphenylsilyloxy]methyl}-1-[5,6,7-trideoxy-2,3-O-isopropylidene-7-C-(triethylsilyl)-β-D-ribo-hept-6-ynofuranosyl]uracil

: 928034-58-6
6-{[(tert-butyl)diphenylsilyloxy]methyl}-1-[5,6,7-trideoxy-2,3-O-isopropylidene-β-D-ribo-hept-6-ynofuranosyl]uracil

Guidance literature:: Multi-step reaction with 2 steps

1: 67 mg / Bu₄NF*3H₂O / tetrahydrofuran / 2 h / 25 °C

2: 106 mg / 1H-imidazole; DMAP / CH₂Cl₂ / 12 h / 25 °C

With 1H-imidazole; dmap; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;
DOI:10.1002/hlca.200690259

Reference yield:

: 928034-56-4
6-{[(tert-butyl)diphenylsilyloxy]methyl}-1-[5,6,7-trideoxy-2,3-O-isopropylidene-7-C-(triethylsilyl)-β-D-allo//α-L-talo-hept-6-ynofuranosyl]uracil

: 928034-58-6
6-{[(tert-butyl)diphenylsilyloxy]methyl}-1-[5,6,7-trideoxy-2,3-O-isopropylidene-β-D-ribo-hept-6-ynofuranosyl]uracil

Guidance literature:: Multi-step reaction with 4 steps

1: 296 mg / CH₂Cl₂ / 30 h

2: 200 mg / Bu₃SnH; AIBN / toluene / 1.5 h / 80 °C

3: 67 mg / Bu₄NF*3H₂O / tetrahydrofuran / 2 h / 25 °C

4: 106 mg / 1H-imidazole; DMAP / CH₂Cl₂ / 12 h / 25 °C

With 1H-imidazole; dmap; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; In tetrahydrofuran; dichloromethane; toluene; 2: Barton-McCombie deoxygenation;
DOI:10.1002/hlca.200690259