(3S)-1-(2'-hydroxy-5'-(hydroxymethyl)phenyl)-3,7-dimethyloct-6-ene-1,3-diol

Base Information

Chemical Name:(3S)-1-(2'-hydroxy-5'-(hydroxymethyl)phenyl)-3,7-dimethyloct-6-ene-1,3-diol
CAS No.:1326774-96-2
Molecular Formula:C₁₇H₂₆O₄
Molecular Weight:294.391
Hs Code.:

Synonyms:(3S)-1-(2'-hydroxy-5'-(hydroxymethyl)phenyl)-3,7-dimethyloct-6-ene-1,3-diol

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Chemical Property of (3S)-1-(2'-hydroxy-5'-(hydroxymethyl)phenyl)-3,7-dimethyloct-6-ene-1,3-diol

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Technology Process of (3S)-1-(2'-hydroxy-5'-(hydroxymethyl)phenyl)-3,7-dimethyloct-6-ene-1,3-diol

There total 11 articles about (3S)-1-(2'-hydroxy-5'-(hydroxymethyl)phenyl)-3,7-dimethyloct-6-ene-1,3-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: 78.0%

: 1326774-95-1
(3S)-3-((tert-butyldimethylsilyl)oxy)-3,7-dimethyl-1-[2'-((2''-(trimethylsilyl)ethoxy)methoxy)-5'-(((2''-(trimethylsilyl)ethoxy)methoxy)methyl)phenyl]oct-6-en-1-ol

: 1326774-96-2
(3S)-1-(2'-hydroxy-5'-(hydroxymethyl)phenyl)-3,7-dimethyloct-6-ene-1,3-diol

Guidance literature:: (3S)-3-((tert-butyldimethylsilyl)oxy)-3,7-dimethyl-1-[2'-((2''-(trimethylsilyl)ethoxy)methoxy)-5'-(((2''-(trimethylsilyl)ethoxy)methoxy)methyl)phenyl]oct-6-en-1-ol; With tetrabutyl ammonium fluoride; In 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; at 80 ℃; for 7h; Molecular sieve;

With water; In 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; diethyl ether; at 20 ℃;
DOI:10.1016/j.tet.2011.06.015

Reference yield:

: 888481-18-3
(3S)-3-(tert-butyl-dimethyl-silanyloxy)-3,7-dimethyl-oct-6-enal

: 1326774-96-2
(3S)-1-(2'-hydroxy-5'-(hydroxymethyl)phenyl)-3,7-dimethyloct-6-ene-1,3-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: tert.-butyl lithium / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

1.2: -78 °C

2.1: tetrabutyl ammonium fluoride / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 7 h / 80 °C / Molecular sieve

2.2: 20 °C

With tetrabutyl ammonium fluoride; tert.-butyl lithium; In tetrahydrofuran; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone;
DOI:10.1016/j.tet.2011.06.015

Reference yield:

: 888481-17-2
(3S)-3-((tert-butyldimethylsilanyl)oxy)-3,7-dimethyloct-6-en-1-ol

: 1326774-96-2
(3S)-1-(2'-hydroxy-5'-(hydroxymethyl)phenyl)-3,7-dimethyloct-6-ene-1,3-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / 3 h / 20 °C

2.1: tert.-butyl lithium / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

2.2: -78 °C

3.1: tetrabutyl ammonium fluoride / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 7 h / 80 °C / Molecular sieve

3.2: 20 °C

With tetrabutyl ammonium fluoride; tert.-butyl lithium; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone;
DOI:10.1016/j.tet.2011.06.015