1-(4-bromophenyl)-5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose

Base Information

• Chemical Name: 1-(4-bromophenyl)-5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose
• CAS No.: 179762-64-2
• Molecular Formula: C₃₀H₃₅BrO₅Si
• Molecular Weight: 583.594

Synonyms:1-(4-bromophenyl)-5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose

Chemical Property of 1-(4-bromophenyl)-5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose

Chemical Property:

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Technology Process of 1-(4-bromophenyl)-5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose

There total 3 articles about 1-(4-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: 87.0%

1.4-dibromobenzene (106-37-6) + 5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone (130222-84-3) → 1-(4-bromophenyl)-5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose (179762-64-2)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 0 ℃;

DOI:10.1021/jo052413u

Reference yield:

1,4-bromoiodobenzene (589-87-7) + 5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone (130222-84-3) → 1-(4-bromophenyl)-5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose (179762-64-2)

Guidance literature:

With n-butyllithium; Multistep reaction; 1.) ether/hexane, RT, 40 min, 2.) ether/hexane/THF, 1 h, -78 deg C;

DOI:10.1016/0040-4039(96)01576-6

Reference yield:

4-bromophenyllithium (22480-64-4) + 5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone (130222-84-3) → 1-(4-bromophenyl)-5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose (179762-64-2)

Guidance literature:

upstream raw materials:

1.4-dibromobenzene

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

1,4-bromoiodobenzene

4-bromophenyllithium

Downstream raw materials:

1-Deoxy-1-[p-(N-TFA)aminophenyl]-β-D-ribofuranose

2,2,2-Trifluoro-N-[4-((3aS,4S,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-phenyl]-acetamide

5-O-t-Butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-1-(p-aminophenyl)-β-D-ribofuranose

N-{4-[(3aS,4S,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-phenyl}-2,2,2-trifluoro-acetamide

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