2-((1R,2R,3S,4S,5S,6R)-3-(benzyloxy)-2,4,5-trihydroxy-6-nitrocyclohexyl)-3-hydroxynaphthalene-1,4-dione

Base Information

Chemical Name:2-((1R,2R,3S,4S,5S,6R)-3-(benzyloxy)-2,4,5-trihydroxy-6-nitrocyclohexyl)-3-hydroxynaphthalene-1,4-dione
CAS No.:1356060-40-6
Molecular Formula:C₂₃H₂₁NO₉
Molecular Weight:455.421
Hs Code.:

Synonyms:2-((1R,2R,3S,4S,5S,6R)-3-(benzyloxy)-2,4,5-trihydroxy-6-nitrocyclohexyl)-3-hydroxynaphthalene-1,4-dione

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Chemical Property of 2-((1R,2R,3S,4S,5S,6R)-3-(benzyloxy)-2,4,5-trihydroxy-6-nitrocyclohexyl)-3-hydroxynaphthalene-1,4-dione

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Technology Process of 2-((1R,2R,3S,4S,5S,6R)-3-(benzyloxy)-2,4,5-trihydroxy-6-nitrocyclohexyl)-3-hydroxynaphthalene-1,4-dione

There total 4 articles about 2-((1R,2R,3S,4S,5S,6R)-3-(benzyloxy)-2,4,5-trihydroxy-6-nitrocyclohexyl)-3-hydroxynaphthalene-1,4-dione 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:

: 3-O-benzyl-5,6-dideoxy-5-C-(3'-hydroxy-1',4'-naphthoquinon-2'-yl)-6-nitro-D-glucofuranose

: 1356060-40-6
2-((1R,2R,3S,4S,5S,6R)-3-(benzyloxy)-2,4,5-trihydroxy-6-nitrocyclohexyl)-3-hydroxynaphthalene-1,4-dione

Guidance literature:: With sodium carbonate; In methanol; water; at 20 ℃; for 12h; diastereoselective reaction;
DOI:10.1016/j.tet.2011.11.072

Reference yield:

: 1356060-39-3
3-O-benzyl-5,6-dideoxy-5-C-(3'-hydroxy-1',4'-naphthoquinon-2'-yl)-1,2-O-isopropylidene-6-nitro-α-D-glucofuranose

: 1356060-40-6
2-((1R,2R,3S,4S,5S,6R)-3-(benzyloxy)-2,4,5-trihydroxy-6-nitrocyclohexyl)-3-hydroxynaphthalene-1,4-dione

Guidance literature:: Multi-step reaction with 2 steps

1: water; trifluoroacetic acid / dichloromethane / 5 h / 20 °C

2: sodium carbonate / methanol; water / 12 h / 20 °C

With water; sodium carbonate; trifluoroacetic acid; In methanol; dichloromethane; water; 2: Henry reaction;
DOI:10.1016/j.tet.2011.11.072

Reference yield:

: 69177-83-9,78283-50-8,86495-59-2,114181-97-4,141782-01-6,51173-35-4
3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-6-nitro-α-D-xylo-hex-5-enofuranose

: 1356060-40-6
2-((1R,2R,3S,4S,5S,6R)-3-(benzyloxy)-2,4,5-trihydroxy-6-nitrocyclohexyl)-3-hydroxynaphthalene-1,4-dione

Guidance literature:: Multi-step reaction with 3 steps

1.1: potassium carbonate / tetrahydrofuran / 35 h / 20 °C / Inert atmosphere

1.2: 20 °C

2.1: water; trifluoroacetic acid / dichloromethane / 5 h / 20 °C

3.1: sodium carbonate / methanol; water / 12 h / 20 °C

With water; sodium carbonate; potassium carbonate; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; 1.1: Michael addition / 3.1: Henry reaction;
DOI:10.1016/j.tet.2011.11.072