(1R,2S,3S,4R,5S,6S)-6-amino-3-(benzyloxy)-1,2,4-trihydroxy-5-(1',4'-naphthoquinon-2'-yl)cyclohexane

Base Information

Chemical Name:(1R,2S,3S,4R,5S,6S)-6-amino-3-(benzyloxy)-1,2,4-trihydroxy-5-(1',4'-naphthoquinon-2'-yl)cyclohexane
CAS No.:847984-58-1
Molecular Formula:C₂₃H₂₃NO₆
Molecular Weight:409.439
Hs Code.:

Synonyms:(1R,2S,3S,4R,5S,6S)-6-amino-3-(benzyloxy)-1,2,4-trihydroxy-5-(1',4'-naphthoquinon-2'-yl)cyclohexane

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Chemical Property of (1R,2S,3S,4R,5S,6S)-6-amino-3-(benzyloxy)-1,2,4-trihydroxy-5-(1',4'-naphthoquinon-2'-yl)cyclohexane

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Technology Process of (1R,2S,3S,4R,5S,6S)-6-amino-3-(benzyloxy)-1,2,4-trihydroxy-5-(1',4'-naphthoquinon-2'-yl)cyclohexane

There total 7 articles about (1R,2S,3S,4R,5S,6S)-6-amino-3-(benzyloxy)-1,2,4-trihydroxy-5-(1',4'-naphthoquinon-2'-yl)cyclohexane 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%

: 847984-57-0
(1R,2S,3S,4R,5S,6S)-6-amino-3-(benzyloxy)-5-(1',4'-dimethoxynaphthalen-2'-yl)cyclohexane-1,2,4-triol

: 847984-58-1
(1R,2S,3S,4R,5S,6S)-6-amino-3-(benzyloxy)-1,2,4-trihydroxy-5-(1',4'-naphthoquinon-2'-yl)cyclohexane

Guidance literature:: With ammonium cerium(IV) nitrate; In water; acetonitrile; at 0 ℃; for 1h;
DOI:10.1016/j.tetasy.2004.11.045

Reference yield:

: 847984-53-6
3-O-benzyl-5,6-dideoxy-5-C-(1',4'-dimethoxynaphthalen-2'-yl)-1,2-O-isopropylidene-6-nitro-β-L-idofuranose

: 847984-58-1
(1R,2S,3S,4R,5S,6S)-6-amino-3-(benzyloxy)-1,2,4-trihydroxy-5-(1',4'-naphthoquinon-2'-yl)cyclohexane

Guidance literature:: Multi-step reaction with 4 steps

1: trifluoroacetic acid / dioxane; H₂O / 16 h / 50 °C

2: sodium hydrogen carbonate / methanol; H₂O / 24 h / 20 °C

3: 95 percent / hydrogen; Raney nickel / methanol / 3 h / 20 °C / 760 Torr

4: 92 percent / ammonium cerium(IV) nitrate / acetonitrile; H₂O / 1 h / 0 °C

With ammonium cerium(IV) nitrate; hydrogen; nickel; sodium hydrogencarbonate; trifluoroacetic acid; In 1,4-dioxane; methanol; water; acetonitrile; 2: Henry reaction;
DOI:10.1016/j.tetasy.2004.11.045

Reference yield:

: 3-O-benzyl-5,6-dideoxy-5-C-(1',4'-dimethoxynaphthalen-2'-yl)-6-nitro-L-idofuranose

: 847984-58-1
(1R,2S,3S,4R,5S,6S)-6-amino-3-(benzyloxy)-1,2,4-trihydroxy-5-(1',4'-naphthoquinon-2'-yl)cyclohexane

Guidance literature:: Multi-step reaction with 3 steps

1: sodium hydrogen carbonate / methanol; H₂O / 24 h / 20 °C

2: 95 percent / hydrogen; Raney nickel / methanol / 3 h / 20 °C / 760 Torr

3: 92 percent / ammonium cerium(IV) nitrate / acetonitrile; H₂O / 1 h / 0 °C

With ammonium cerium(IV) nitrate; hydrogen; nickel; sodium hydrogencarbonate; In methanol; water; acetonitrile; 1: Henry reaction;
DOI:10.1016/j.tetasy.2004.11.045