2-O-[(tert-butyl)dimethylsilyl]-1-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-1-(3-fluorophenyl)-β-D-ribofuranose

Base Information

Chemical Name:2-O-[(tert-butyl)dimethylsilyl]-1-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-1-(3-fluorophenyl)-β-D-ribofuranose
CAS No.:304436-65-5
Molecular Formula:C₃₈H₄₅FO₆Si
Molecular Weight:644.856
Hs Code.:

Synonyms:2-O-[(tert-butyl)dimethylsilyl]-1-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-1-(3-fluorophenyl)-β-D-ribofuranose

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Chemical Property of 2-O-[(tert-butyl)dimethylsilyl]-1-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-1-(3-fluorophenyl)-β-D-ribofuranose

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Technology Process of 2-O-[(tert-butyl)dimethylsilyl]-1-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-1-(3-fluorophenyl)-β-D-ribofuranose

There total 6 articles about 2-O-[(tert-butyl)dimethylsilyl]-1-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-1-(3-fluorophenyl)-β-D-ribofuranose 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: 42.5%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 304436-64-4
1-deoxy-5-O-(4,4'-dimethoxytrityl)-1-(3-fluorophenyl)-β-D-ribofuranose

: 304436-65-5
2-O-[(tert-butyl)dimethylsilyl]-1-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-1-(3-fluorophenyl)-β-D-ribofuranose

: 3-O-[(tert-butyl)dimethylsilyl]-1-deoxy-5-O-(4,4'-dimethoxytrityl)-1-(3-fluorophenyl)-β-D-ribofuranose

Guidance literature:: With silver nitrate; In tetrahydrofuran; pyridine; at 20 ℃; for 20h;
DOI:10.1002/1522-2675(20000809)83:8<1791::AID-HLCA1791>3.0.CO;2-K

Reference yield:

: 1073-06-9
3-fluorobromobenzene

: 304436-65-5
2-O-[(tert-butyl)dimethylsilyl]-1-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-1-(3-fluorophenyl)-β-D-ribofuranose

Guidance literature:: Multi-step reaction with 5 steps

1: BuLi / tetrahydrofuran; hexane / 3 h / -78 - -30 °C

2: BF₃*Et₂O; Et₃SiH / CH₂Cl₂ / 1 h / -78 °C

3: 96.7 percent / cyclohexene / 20 percent Pd(OH)2/C / ethanol / 3 h / Heating

4: 96.4 percent / Et₃N / pyridine / 4 h / 20 °C

5: 33.1 percent / AgNO₃ / tetrahydrofuran; pyridine / 20 h / 20 °C

With triethylsilane; n-butyllithium; boron trifluoride diethyl etherate; silver nitrate; triethylamine; cyclohexene; palladium dihydroxide; In tetrahydrofuran; pyridine; ethanol; hexane; dichloromethane; 1: Dehydrogenation / 2: dehydroxylation / 3: Catalytic hydrogenation / 4: Etherification / 5: Etherification;
DOI:10.1002/1522-2675(20000809)83:8<1791::AID-HLCA1791>3.0.CO;2-K

Reference yield:

: 14233-64-8,134307-32-7,55094-52-5
(3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-dihydro-furan-2-one

: 304436-65-5
2-O-[(tert-butyl)dimethylsilyl]-1-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-1-(3-fluorophenyl)-β-D-ribofuranose

Guidance literature:: Multi-step reaction with 5 steps

1: BuLi / tetrahydrofuran; hexane / 3 h / -78 - -30 °C

2: BF₃*Et₂O; Et₃SiH / CH₂Cl₂ / 1 h / -78 °C

3: 96.7 percent / cyclohexene / 20 percent Pd(OH)2/C / ethanol / 3 h / Heating

4: 96.4 percent / Et₃N / pyridine / 4 h / 20 °C

5: 33.1 percent / AgNO₃ / tetrahydrofuran; pyridine / 20 h / 20 °C

With triethylsilane; n-butyllithium; boron trifluoride diethyl etherate; silver nitrate; triethylamine; cyclohexene; palladium dihydroxide; In tetrahydrofuran; pyridine; ethanol; hexane; dichloromethane; 1: Dehydrogenation / 2: dehydroxylation / 3: Catalytic hydrogenation / 4: Etherification / 5: Etherification;
DOI:10.1002/1522-2675(20000809)83:8<1791::AID-HLCA1791>3.0.CO;2-K