1,2-O-isopropylidene-3-O-benzoyl-(E)-3-(diethylphosphono)vinyl-α-D-erythrofuranose

Base Information

Chemical Name:1,2-O-isopropylidene-3-O-benzoyl-(E)-3-(diethylphosphono)vinyl-α-D-erythrofuranose
CAS No.:1293981-90-4
Molecular Formula:C₂₀H₂₇O₈P
Molecular Weight:426.403
Hs Code.:

Synonyms:1,2-O-isopropylidene-3-O-benzoyl-(E)-3-(diethylphosphono)vinyl-α-D-erythrofuranose

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Chemical Property of 1,2-O-isopropylidene-3-O-benzoyl-(E)-3-(diethylphosphono)vinyl-α-D-erythrofuranose

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Technology Process of 1,2-O-isopropylidene-3-O-benzoyl-(E)-3-(diethylphosphono)vinyl-α-D-erythrofuranose

There total 6 articles about 1,2-O-isopropylidene-3-O-benzoyl-(E)-3-(diethylphosphono)vinyl-α-D-erythrofuranose 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: 92.0%

: 1293981-89-1
1,2-O-isopropylidene-(E)-3-(diethylphosphono)vinyl-α-D-erythrofuranose

: 98-88-4
benzoyl chloride

: 1293981-90-4
1,2-O-isopropylidene-3-O-benzoyl-(E)-3-(diethylphosphono)vinyl-α-D-erythrofuranose

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1021/jo200033p

Reference yield:

: 34693-28-2
(3aR,6aS)-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-6(5H)-one

: 1293981-90-4
1,2-O-isopropylidene-3-O-benzoyl-(E)-3-(diethylphosphono)vinyl-α-D-erythrofuranose

Guidance literature:: Multi-step reaction with 3 steps

1.1: cerium(III) chloride / tetrahydrofuran / 1.83 h / -78 °C / Inert atmosphere

1.2: -78 °C / Inert atmosphere

2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / Inert atmosphere; Reflux

3.1: dmap; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; cerium(III) chloride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo200033p

Reference yield:

: 1,2-O-isopropylidene-5-O-(N-phthalimido)-α-D-xylofuranose

: 1293981-90-4
1,2-O-isopropylidene-3-O-benzoyl-(E)-3-(diethylphosphono)vinyl-α-D-erythrofuranose

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 3 h / 80 °C / Inert atmosphere

2.1: pyridinium chlorochromate / dichloromethane / 0 - 20 °C / Molecular sieve; Inert atmosphere

3.1: cerium(III) chloride / tetrahydrofuran / 1.83 h / -78 °C / Inert atmosphere

3.2: -78 °C / Inert atmosphere

4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / Inert atmosphere; Reflux

5.1: dmap; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; cerium(III) chloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jo200033p