3,5-di-O-benzyl-4-C-(2,2-dibromoethenyl)-1,2-O-isopropylidene-α-D-ribo-pentofuranose

Base Information

Chemical Name:3,5-di-O-benzyl-4-C-(2,2-dibromoethenyl)-1,2-O-isopropylidene-α-D-ribo-pentofuranose
CAS No.:233266-77-8
Molecular Formula:C₂₄H₂₆Br₂O₅
Molecular Weight:554.275
Hs Code.:

Synonyms:3,5-di-O-benzyl-4-C-(2,2-dibromoethenyl)-1,2-O-isopropylidene-α-D-ribo-pentofuranose

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Chemical Property of 3,5-di-O-benzyl-4-C-(2,2-dibromoethenyl)-1,2-O-isopropylidene-α-D-ribo-pentofuranose

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Technology Process of 3,5-di-O-benzyl-4-C-(2,2-dibromoethenyl)-1,2-O-isopropylidene-α-D-ribo-pentofuranose

There total 5 articles about 3,5-di-O-benzyl-4-C-(2,2-dibromoethenyl)-1,2-O-isopropylidene-α-D-ribo-pentofuranose 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: 95.4%

: 558-13-4
carbon tetrabromide

: 233266-76-7
(3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde

: 233266-77-8
3,5-di-O-benzyl-4-C-(2,2-dibromoethenyl)-1,2-O-isopropylidene-α-D-ribo-pentofuranose

Guidance literature:: With triphenylphosphine; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/jm000209n

Reference yield:

: 153186-10-8
((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

: 233266-77-8
3,5-di-O-benzyl-4-C-(2,2-dibromoethenyl)-1,2-O-isopropylidene-α-D-ribo-pentofuranose

Guidance literature:: Multi-step reaction with 2 steps

1: 94.6 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 1 h / -60 - 20 °C

2: 95.4 percent / triphenylphosphine / CH₂Cl₂ / 1 h / 0 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; triphenylphosphine; In dichloromethane; 1: Swern oxidation;
DOI:10.1021/jm000209n

Reference yield:

: (3aR,5S,6S,6aR)-6-benzyloxy-5-(benzyloxymethyl)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[2,3-d][1,3]dioxole

: 233266-77-8
3,5-di-O-benzyl-4-C-(2,2-dibromoethenyl)-1,2-O-isopropylidene-α-D-ribo-pentofuranose

Guidance literature:: Multi-step reaction with 2 steps

1.1: iodine; sodium periodate / water; acetonitrile / 2 h / 70 °C

2.1: triphenylphosphine / dichloromethane / 0.5 h / 0 °C

2.2: 1.08 h / 0 °C

With sodium periodate; iodine; triphenylphosphine; In dichloromethane; water; acetonitrile;
DOI:10.1021/ol5036535