(5S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-5-methyl-heptan-2-one

Base Information

Chemical Name:(5S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-5-methyl-heptan-2-one
CAS No.:743472-16-4
Molecular Formula:C₂₂H₃₈O₄Si
Molecular Weight:394.627
Hs Code.:

Synonyms:(5S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-5-methyl-heptan-2-one

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Chemical Property of (5S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-5-methyl-heptan-2-one

Chemical Property:

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Technology Process of (5S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-5-methyl-heptan-2-one

There total 6 articles about (5S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-5-methyl-heptan-2-one 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:

: 743472-05-1
(E)-(5S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-5-methyl-hept-3-en-2-one

: 743472-16-4
(5S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-5-methyl-heptan-2-one

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol;
DOI:10.1021/ol0491078

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 743472-16-4
(5S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-5-methyl-heptan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 2,6-lutidine / CH₂Cl₂ / 0.25 h / 25 °C

2: DIBALH / CH₂Cl₂ / 0.5 h / 0 °C

3: LiCl; DIPEA / acetonitrile / 25 °C

4: H₂ / Pd/C / methanol

With 2,6-dimethylpyridine; hydrogen; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium on activated charcoal; In methanol; dichloromethane; acetonitrile; 3: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ol0491078

Reference yield:

: 121289-23-4
p-methoxybenzyloxyacetaldehyde

: 743472-16-4
(5S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-5-methyl-heptan-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-Bu₂BOTf; Et₃N / CH₂Cl₂ / -5 °C

1.2: 94 percent / CH₂Cl₂ / 3 h / -78 °C

2.1: Me₃Al / tetrahydrofuran / 2 h / 0 °C

3.1: 2,6-lutidine / CH₂Cl₂ / 0.25 h / 25 °C

4.1: DIBALH / CH₂Cl₂ / 0.5 h / 0 °C

5.1: LiCl; DIPEA / acetonitrile / 25 °C

6.1: H₂ / Pd/C / methanol

With 2,6-dimethylpyridine; di-n-butylboryl trifluoromethanesulfonate; hydrogen; trimethylaluminum; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 5.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ol0491078