(3S,5S,6R)-1-(4-methoxy-benzyloxy)-5-methoxymethoxy-6,9-dimethyl-dec-8-en-3-ol

Base Information

Chemical Name:(3S,5S,6R)-1-(4-methoxy-benzyloxy)-5-methoxymethoxy-6,9-dimethyl-dec-8-en-3-ol
CAS No.:312962-20-2
Molecular Formula:C₂₂H₃₆O₅
Molecular Weight:380.525
Hs Code.:

Synonyms:(3S,5S,6R)-1-(4-methoxy-benzyloxy)-5-methoxymethoxy-6,9-dimethyl-dec-8-en-3-ol

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Chemical Property of (3S,5S,6R)-1-(4-methoxy-benzyloxy)-5-methoxymethoxy-6,9-dimethyl-dec-8-en-3-ol

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Technology Process of (3S,5S,6R)-1-(4-methoxy-benzyloxy)-5-methoxymethoxy-6,9-dimethyl-dec-8-en-3-ol

There total 10 articles about (3S,5S,6R)-1-(4-methoxy-benzyloxy)-5-methoxymethoxy-6,9-dimethyl-dec-8-en-3-ol 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: 85.0%

: 824-94-2
p-methoxybenzyl chloride

: 312962-19-9
(3S,5S,6R)-5-methoxymethoxy-6,9-dimethyl-dec-8-ene-1,3-diol

: 312962-20-2
(3S,5S,6R)-1-(4-methoxy-benzyloxy)-5-methoxymethoxy-6,9-dimethyl-dec-8-en-3-ol

Guidance literature:: (3S,5S,6R)-5-methoxymethoxy-6,9-dimethyl-dec-8-ene-1,3-diol; With sodium hydride; In N,N-dimethyl-formamide; for 1.25h;

p-methoxybenzyl chloride; In N,N-dimethyl-formamide; for 1.5h; Further stages.;
DOI:10.1021/ol006646d

Reference yield:

: 870-63-3
prenyl bromide

: 312962-20-2
(3S,5S,6R)-1-(4-methoxy-benzyloxy)-5-methoxymethoxy-6,9-dimethyl-dec-8-en-3-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

1.2: 85 percent / tetrahydrofuran / 16 h / 0 °C

2.1: 99 percent / LiOH*H₂O; H₂O₂ / tetrahydrofuran / 4 h / 0 °C

3.1: (1-chloro-2-methyl-propenyl)-dimethyl-amine / CH₂Cl₂ / 1.5 h

4.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

4.2: 3.50 g / tetrahydrofuran; hexane / 2 h / 20 °C

5.1: 96 percent / H₂ / [(R)-BINAP*RuCl₂]2*NEt₃ / methanol / 4 h / 80 °C / 3040.2 Torr

6.1: 90 percent / diisopropylethylamine; N,N-dimethylaminopyridine / CH₂Cl₂ / 40 h / 20 °C

7.1: LiHMDS / tetrahydrofuran / 1.5 h / -45 - -30 °C

7.2: 98 percent / tetrahydrofuran / 3 h / -40 - -30 °C

8.1: 93 percent / H₂ / [(R)-BINAP*RuCl₂]*NEt₃ / methanol / 6.5 h / 25 °C / 60804.1 Torr

9.1: 98 percent / LiAlH₄ / diethyl ether / 6 h / 0 °C

10.1: NaH / dimethylformamide / 1.25 h

10.2: 85 percent / dimethylformamide / 1.5 h

With dmap; lithium hydroxide; lithium aluminium tetrahydride; n-butyllithium; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; hydrogen; dihydrogen peroxide; sodium hydride; diisopropylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; [(R)-BINAP RuCl₂]2NEt₃; [(R)-BINAP*RuCl₂]*NEt₃; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Substitution / 2.1: Hydrolysis / 3.1: Substitution / 4.1: deprotonation / 4.2: Substitution / 5.1: Catalytic hydrogenation / 6.1: Alkylation / 7.1: Metallation / 7.2: Metallation / 8.1: Catalytic hydrogenation / 9.1: Reduction / 10.1: deprotonation / 10.2: Alkylation;
DOI:10.1021/ol006646d

Reference yield:

: 312962-13-3
(2R)-2,5-dimethyl-hex-4-enoyl chloride

: 312962-20-2
(3S,5S,6R)-1-(4-methoxy-benzyloxy)-5-methoxymethoxy-6,9-dimethyl-dec-8-en-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: 3.50 g / tetrahydrofuran; hexane / 2 h / 20 °C

2.1: 96 percent / H₂ / [(R)-BINAP*RuCl₂]2*NEt₃ / methanol / 4 h / 80 °C / 3040.2 Torr

3.1: 90 percent / diisopropylethylamine; N,N-dimethylaminopyridine / CH₂Cl₂ / 40 h / 20 °C

4.1: LiHMDS / tetrahydrofuran / 1.5 h / -45 - -30 °C

4.2: 98 percent / tetrahydrofuran / 3 h / -40 - -30 °C

5.1: 93 percent / H₂ / [(R)-BINAP*RuCl₂]*NEt₃ / methanol / 6.5 h / 25 °C / 60804.1 Torr

6.1: 98 percent / LiAlH₄ / diethyl ether / 6 h / 0 °C

7.1: NaH / dimethylformamide / 1.25 h

7.2: 85 percent / dimethylformamide / 1.5 h

With dmap; lithium aluminium tetrahydride; n-butyllithium; hydrogen; sodium hydride; diisopropylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; [(R)-BINAP RuCl₂]2NEt₃; [(R)-BINAP*RuCl₂]*NEt₃; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: deprotonation / 1.2: Substitution / 2.1: Catalytic hydrogenation / 3.1: Alkylation / 4.1: Metallation / 4.2: Metallation / 5.1: Catalytic hydrogenation / 6.1: Reduction / 7.1: deprotonation / 7.2: Alkylation;
DOI:10.1021/ol006646d