(1R,2R,3S,4R,5R,6R)-2,6-bis(benzyloxy)-4-(3'-hydroxy-1',4'-naphthoquinon-2'-yl)-5-nitrocyclohexane-1,3-diyl diacetate

Base Information

Chemical Name:(1R,2R,3S,4R*,5R*,6R)-2,6-bis(benzyloxy)-4-(3'-hydroxy-1',4'-naphthoquinon-2'-yl)-5-nitrocyclohexane-1,3-diyl diacetate
CAS No.:1356060-38-2
Molecular Formula:C₃₄H₃₁NO₁₁
Molecular Weight:629.62
Hs Code.:

Synonyms:(1R,2R,3S,4R*,5R*,6R)-2,6-bis(benzyloxy)-4-(3'-hydroxy-1',4'-naphthoquinon-2'-yl)-5-nitrocyclohexane-1,3-diyl diacetate

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Chemical Property of (1R,2R,3S,4R*,5R*,6R)-2,6-bis(benzyloxy)-4-(3'-hydroxy-1',4'-naphthoquinon-2'-yl)-5-nitrocyclohexane-1,3-diyl diacetate

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Technology Process of (1R,2R,3S,4R*,5R*,6R)-2,6-bis(benzyloxy)-4-(3'-hydroxy-1',4'-naphthoquinon-2'-yl)-5-nitrocyclohexane-1,3-diyl diacetate

There total 5 articles about (1R,2R,3S,4R*,5R*,6R)-2,6-bis(benzyloxy)-4-(3'-hydroxy-1',4'-naphthoquinon-2'-yl)-5-nitrocyclohexane-1,3-diyl diacetate 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: 57.0%

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

: 1356060-37-1
(1R,2R,3S,6R)-2,6-bis(benzyloxy)-5-nitrocyclohex-4-ene-1,3-diyl diacetate

: 1356060-38-2
(1R,2R,3S,4R*,5R*,6R)-2,6-bis(benzyloxy)-4-(3'-hydroxy-1',4'-naphthoquinon-2'-yl)-5-nitrocyclohexane-1,3-diyl diacetate

Guidance literature:: 2-hydroxynaphtho-1,4-quinone; (1R,2R,3S,6R)-2,6-bis(benzyloxy)-5-nitrocyclohex-4-ene-1,3-diyl diacetate; With potassium carbonate; In tetrahydrofuran; at 20 ℃; for 16h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; water; at 20 ℃;
DOI:10.1016/j.tet.2011.11.072

Reference yield:

: 3,5-di-O-benzyl-6-deoxy-6-nitro-D-glucofuranose

: 1356060-38-2
(1R,2R,3S,4R*,5R*,6R)-2,6-bis(benzyloxy)-4-(3'-hydroxy-1',4'-naphthoquinon-2'-yl)-5-nitrocyclohexane-1,3-diyl diacetate

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydrogencarbonate / methanol; water / 14 h / 20 °C

2.1: dmap / diethyl ether / 1 h / 0 °C / Inert atmosphere

3.1: potassium carbonate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

3.2: 20 °C

With dmap; sodium hydrogencarbonate; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; water; 1.1: Henry reaction / 3.1: Michael addition;
DOI:10.1016/j.tet.2011.11.072

Reference yield:

: C₂₀H₂₃NO₇

: 1356060-38-2
(1R,2R,3S,4R*,5R*,6R)-2,6-bis(benzyloxy)-4-(3'-hydroxy-1',4'-naphthoquinon-2'-yl)-5-nitrocyclohexane-1,3-diyl diacetate

Guidance literature:: Multi-step reaction with 2 steps

1.1: dmap / diethyl ether / 1 h / 0 °C / Inert atmosphere

2.1: potassium carbonate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

2.2: 20 °C

With dmap; potassium carbonate; In tetrahydrofuran; diethyl ether; 2.1: Michael addition;
DOI:10.1016/j.tet.2011.11.072