(-)-(R)-13-cis-3-hydroxyretinal

Base Information

Chemical Name:(-)-(R)-13-cis-3-hydroxyretinal
CAS No.:875927-53-0
Molecular Formula:C₂₀H₂₈O₂
Molecular Weight:300.441
Hs Code.:

Synonyms:(-)-(R)-13-cis-3-hydroxyretinal

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Chemical Property of (-)-(R)-13-cis-3-hydroxyretinal

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Technology Process of (-)-(R)-13-cis-3-hydroxyretinal

There total 8 articles about (-)-(R)-13-cis-3-hydroxyretinal 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:

: 152187-06-9
(R)-5-(tert-butyldimethylsilyloxy)-2-[(trifluoromethanesulfonyl)oxy]-1,3,3-trimethylcyclohex-1-ene

: 875927-53-0,7584-74-9
(-)-(R)-13-cis-3-hydroxyretinal

Guidance literature:: Multi-step reaction with 6 steps

1.1: 68 percent / AsPh₃; LiCl / Pd₂(dba)3 / 1-methyl-pyrrolidin-2-one / 14 h / 80 °C

2.1: 83 percent / N-methylmorpholine N-oxide; 4 Angstroem molecular sieves; tetra-n-propylammonium perruthenate / CH₂Cl₂ / 3 h / 25 °C

3.1: DMPU; n-BuLi / tetrahydrofuran; hexane / 0.5 h

3.2: 99 percent / tetrahydrofuran; hexane / 14 h / -78 - 25 °C

4.1: 58 percent / n-Bu₄NF / tetrahydrofuran / 7 h / 25 °C

5.1: 66 percent / Dibal-H / hexane; tetrahydrofuran / 1 h / -78 °C

6.1: MnO₂; Na₂CO₃ / CH₂Cl₂ / 5 h / 25 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; manganese(IV) oxide; n-butyllithium; tetrapropylammonium perruthennate; triphenyl-arsane; 4 A molecular sieve; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; sodium carbonate; 4-methylmorpholine N-oxide; lithium chloride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; hexane; dichloromethane; 1.1: Stille cross coupling / 3.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1039/b514273c

Reference yield:

: 128426-10-8
(2E,4E)-5-(tri-n-butylstannyl)-3-methylpenta-2,4-dien-1-ol

: 875927-53-0,7584-74-9
(-)-(R)-13-cis-3-hydroxyretinal

Guidance literature:: Multi-step reaction with 6 steps

1.1: 68 percent / AsPh₃; LiCl / Pd₂(dba)3 / 1-methyl-pyrrolidin-2-one / 14 h / 80 °C

2.1: 83 percent / N-methylmorpholine N-oxide; 4 Angstroem molecular sieves; tetra-n-propylammonium perruthenate / CH₂Cl₂ / 3 h / 25 °C

3.1: DMPU; n-BuLi / tetrahydrofuran; hexane / 0.5 h

3.2: 99 percent / tetrahydrofuran; hexane / 14 h / -78 - 25 °C

4.1: 58 percent / n-Bu₄NF / tetrahydrofuran / 7 h / 25 °C

5.1: 66 percent / Dibal-H / hexane; tetrahydrofuran / 1 h / -78 °C

6.1: MnO₂; Na₂CO₃ / CH₂Cl₂ / 5 h / 25 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; manganese(IV) oxide; n-butyllithium; tetrapropylammonium perruthennate; triphenyl-arsane; 4 A molecular sieve; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; sodium carbonate; 4-methylmorpholine N-oxide; lithium chloride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; hexane; dichloromethane; 1.1: Stille cross coupling / 3.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1039/b514273c