1-(2-bromophenyl)-5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose

Base Information

Chemical Name:1-(2-bromophenyl)-5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose
CAS No.:881423-76-3
Molecular Formula:C₃₀H₃₅BrO₅Si
Molecular Weight:583.594
Hs Code.:

Synonyms:1-(2-bromophenyl)-5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose

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Chemical Property of 1-(2-bromophenyl)-5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose

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Technology Process of 1-(2-bromophenyl)-5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose

There total 1 articles about 1-(2-bromophenyl)-5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-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: 100.0%

: 130222-84-3
5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone

: 583-53-9
2,3-dibromobenzene

: 881423-76-3
1-(2-bromophenyl)-5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose

Guidance literature:: With n-butyllithium; In tetrahydrofuran; diethyl ether; hexane; at -110 ℃; for 3.5h;
DOI:10.1021/jo052413u

Reference yield:

: 881423-76-3
1-(2-bromophenyl)-5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose

: (3aS,5R,6R,6aR)-3a-(2-Bromo-phenyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-hexahydro-furo[3,2-b]furan-2,6-diol

Guidance literature:: Multi-step reaction with 3 steps

1: ZnBr₂ / nitromethane / 0 - 20 °C

2: OsO₄; NaIO₄; pyridine / H₂O / 30 h / 20 °C

3: H₂SO₄ / tetrahydrofuran; H₂O / 12 h / 60 °C

With pyridine; sodium periodate; osmium(VIII) oxide; sulfuric acid; zinc dibromide; In tetrahydrofuran; nitromethane; water;
DOI:10.1021/jo052413u

Reference yield:

: 881423-76-3
1-(2-bromophenyl)-5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose

: Diisopropyl-phosphoramidous acid (2R,3R,3aR,5S,6aS)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-6a-(2-bromo-phenyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-hexahydro-furo[3,2-b]furan-3-yl ester 2-cyano-ethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: ZnBr₂ / nitromethane / 0 - 20 °C

2: OsO₄; NaIO₄; pyridine / H₂O / 30 h / 20 °C

3: H₂SO₄ / tetrahydrofuran; H₂O / 12 h / 60 °C

4: 663 mg / pyridine / 0 - 20 °C

5: 62 percent / trimethylsilyl N-(trimethylsilyl)acetimidate; TMSOTf / acetonitrile / 1 h / 20 °C

6: TBAF / tetrahydrofuran / 20 °C

7: 99 percent / NaOH / tetrahydrofuran; methanol; H₂O / 0 °C

8: pyridine / 1 h

9: i-Pr₂NEt / CH₂Cl₂ / 1 h / 0 °C

With pyridine; sodium hydroxide; sodium periodate; osmium(VIII) oxide; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; zinc dibromide; In tetrahydrofuran; methanol; nitromethane; dichloromethane; water; acetonitrile;
DOI:10.1021/jo052413u