1D-(1,2,4/3)-2,3,4-Tri-O-benzyl-5-C-(hydroxymethyl)-5-cyclohexen-1,2,3,4-tetrol

Base Information

Chemical Name:1D-(1,2,4/3)-2,3,4-Tri-O-benzyl-5-C-(hydroxymethyl)-5-cyclohexen-1,2,3,4-tetrol
CAS No.:105017-77-4
Molecular Formula:C₂₈H₃₀O₅
Molecular Weight:446.543
Hs Code.:

Synonyms:1D-(1,2,4/3)-2,3,4-Tri-O-benzyl-5-C-(hydroxymethyl)-5-cyclohexen-1,2,3,4-tetrol

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Chemical Property of 1D-(1,2,4/3)-2,3,4-Tri-O-benzyl-5-C-(hydroxymethyl)-5-cyclohexen-1,2,3,4-tetrol

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Technology Process of 1D-(1,2,4/3)-2,3,4-Tri-O-benzyl-5-C-(hydroxymethyl)-5-cyclohexen-1,2,3,4-tetrol

There total 12 articles about 1D-(1,2,4/3)-2,3,4-Tri-O-benzyl-5-C-(hydroxymethyl)-5-cyclohexen-1,2,3,4-tetrol 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: 78.0%

: 109923-15-1,109959-11-7
(1S,2S,3S,4R)-1-O-benzoyl-5-(benzoyloxymethyl)-2,3,4-tri-O-benzyl-5-cyclohexene-1,2,3,4-tetrol

: 105017-77-4
1D-(1,2,4/3)-2,3,4-Tri-O-benzyl-5-C-(hydroxymethyl)-5-cyclohexen-1,2,3,4-tetrol

Guidance literature:: With sodium methylate; Ambient temperature;
DOI:10.1016/S0008-6215(00)90027-2

Reference yield: 62.0%

: 213400-35-2
(1S,2S,3S,4R)-2,3,4-tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3,4-tetrol

: 105017-77-4
1D-(1,2,4/3)-2,3,4-Tri-O-benzyl-5-C-(hydroxymethyl)-5-cyclohexen-1,2,3,4-tetrol

Guidance literature:: (1S,2S,3S,4R)-2,3,4-tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3,4-tetrol; With acetic anhydride; zinc(II) chloride; In acetic acid; at 20 ℃; for 2h; Inert atmosphere;

With sodium methylate; In methanol; at 20 ℃; for 4h; regioselective reaction; Inert atmosphere;
DOI:10.1039/c0ob00475h

Reference yield:

: 851542-24-0
(2R,3S,4R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)hex-5-enal

: 105017-77-4
1D-(1,2,4/3)-2,3,4-Tri-O-benzyl-5-C-(hydroxymethyl)-5-cyclohexen-1,2,3,4-tetrol

Guidance literature:: Multi-step reaction with 2 steps

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

2.1: acetic anhydride; zinc(II) chloride / acetic acid / 2 h / 20 °C / Inert atmosphere

2.2: 4 h / 20 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; acetic anhydride; zinc(II) chloride; In dichloromethane; acetic acid;
DOI:10.1039/c0ob00475h