(3S,5R)-2-(2,3-dihydroxy-2-methylhept-6-en-5-yl)-5-methylbenzene-1,4-diol

Base Information

Chemical Name:(3S,5R)-2-(2,3-dihydroxy-2-methylhept-6-en-5-yl)-5-methylbenzene-1,4-diol
CAS No.:1398244-25-1
Molecular Formula:C₁₅H₂₂O₄
Molecular Weight:266.337
Hs Code.:

Synonyms:(3S,5R)-2-(2,3-dihydroxy-2-methylhept-6-en-5-yl)-5-methylbenzene-1,4-diol

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Chemical Property of (3S,5R)-2-(2,3-dihydroxy-2-methylhept-6-en-5-yl)-5-methylbenzene-1,4-diol

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Technology Process of (3S,5R)-2-(2,3-dihydroxy-2-methylhept-6-en-5-yl)-5-methylbenzene-1,4-diol

There total 10 articles about (3S,5R)-2-(2,3-dihydroxy-2-methylhept-6-en-5-yl)-5-methylbenzene-1,4-diol 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: 67.0%

: 1340478-34-3
(3S,5R)-5-(2,5-dihydroxy-4-methylphenyl)-2-hydroxy-2-methylhept-6-en-3-yl acetate

: 1398244-25-1
(3S,5R)-2-(2,3-dihydroxy-2-methylhept-6-en-5-yl)-5-methylbenzene-1,4-diol

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at 0 ℃; for 1.5h; Inert atmosphere;
DOI:10.1021/jo3016055

Reference yield:

: 4925-88-6
2,5-dimethoxy-4-methylbenzaldehyde

: 1398244-25-1
(3S,5R)-2-(2,3-dihydroxy-2-methylhept-6-en-5-yl)-5-methylbenzene-1,4-diol

Guidance literature:: Multi-step reaction with 12 steps

1.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / -10 °C / Inert atmosphere

1.2: 0.5 h / 20 °C / Inert atmosphere

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 3.5 h / 20 °C / Inert atmosphere

3.1: hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; potassium hexacyanoferrate(III); potassium carbonate; potassium dioxido(dioxo)osmium hydrate; methanesulfonamide / water; tert-butyl alcohol / 19 h / 0 °C

4.1: triethylamine; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

5.1: potassium carbonate / methanol / 1 h / 20 °C / Inert atmosphere

6.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

6.2: 0.17 h / -78 °C / Inert atmosphere

6.3: 1 h / -78 °C / Inert atmosphere

7.1: quinoline; hydrogen / ethyl acetate / 1 h / 50 °C

8.1: dmap; pyridine / dichloromethane / 5.5 h / 20 °C

9.1: ammonium cerium (IV) nitrate / water; acetonitrile / 0.08 h / 0 °C

10.1: t-butyldimethylsiyl triflate / 0.5 h / -10 °C / Inert atmosphere

11.1: sodium dithionite / tetrahydrofuran; water / 2.5 h / 0 - 20 °C

12.1: diisobutylaluminium hydride / hexane; tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

With pyridine; quinoline; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; sodium dithionite; ammonium cerium (IV) nitrate; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; methanesulfonamide; potassium dioxido(dioxo)osmium hydrate; potassium hexacyanoferrate(III); t-butyldimethylsiyl triflate; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; acetonitrile; tert-butyl alcohol; 10.1: |Hosomi-Sakurai Reaction;
DOI:10.1021/jo3016055

Reference yield:

: 1398244-40-0
(S)-2-(2,5-dimethoxy-4-methylphenoxy)-2-methyl-7-(trimethylsilyl)hept-5-yn-3-ol

: 1398244-25-1
(3S,5R)-2-(2,3-dihydroxy-2-methylhept-6-en-5-yl)-5-methylbenzene-1,4-diol

Guidance literature:: Multi-step reaction with 6 steps

1: quinoline; hydrogen / ethyl acetate / 1 h / 50 °C

2: dmap; pyridine / dichloromethane / 5.5 h / 20 °C

3: ammonium cerium (IV) nitrate / water; acetonitrile / 0.08 h / 0 °C

4: t-butyldimethylsiyl triflate / 0.5 h / -10 °C / Inert atmosphere

5: sodium dithionite / tetrahydrofuran; water / 2.5 h / 0 - 20 °C

6: diisobutylaluminium hydride / hexane; tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

With pyridine; quinoline; dmap; sodium dithionite; ammonium cerium (IV) nitrate; t-butyldimethylsiyl triflate; hydrogen; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; water; ethyl acetate; acetonitrile; 4: |Hosomi-Sakurai Reaction;
DOI:10.1021/jo3016055