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

Base Information

Chemical Name:3-O-benzyl-5,6-dideoxy-5-C-(3'-hydroxy-1',4'-naphthoquinon-2'-yl)-1,2-O-isopropylidene-6-nitro-α-D-glucofuranose
CAS No.:1356060-39-3
Molecular Formula:C₂₆H₂₅NO₉
Molecular Weight:495.486
Hs Code.:

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

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Chemical Property of 3-O-benzyl-5,6-dideoxy-5-C-(3'-hydroxy-1',4'-naphthoquinon-2'-yl)-1,2-O-isopropylidene-6-nitro-α-D-glucofuranose

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Technology Process of 3-O-benzyl-5,6-dideoxy-5-C-(3'-hydroxy-1',4'-naphthoquinon-2'-yl)-1,2-O-isopropylidene-6-nitro-α-D-glucofuranose

There total 1 articles about 3-O-benzyl-5,6-dideoxy-5-C-(3'-hydroxy-1',4'-naphthoquinon-2'-yl)-1,2-O-isopropylidene-6-nitro-α-D-glucofuranose 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: 98.0%

: 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

: 83-72-7
2-hydroxynaphtho-1,4-quinone

: 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

Guidance literature:: 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-6-nitro-α-D-xylo-hex-5-enofuranose; 2-hydroxynaphtho-1,4-quinone; With potassium carbonate; In tetrahydrofuran; at 20 ℃; for 35h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; water; at 20 ℃; optical yield given as %de; 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

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

Guidance literature:: With water; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 5h;
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