(4S,5R,6R,7S)-9-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-4,6-dimethyl-nonan-3-one

Base Information

Chemical Name:(4S,5R,6R,7S)-9-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-4,6-dimethyl-nonan-3-one
CAS No.:82864-88-8
Molecular Formula:C₂₅H₄₄O₄Si
Molecular Weight:436.707
Hs Code.:

Synonyms:(4S,5R,6R,7S)-9-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-4,6-dimethyl-nonan-3-one

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Chemical Property of (4S,5R,6R,7S)-9-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-4,6-dimethyl-nonan-3-one

Chemical Property:

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Technology Process of (4S,5R,6R,7S)-9-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-4,6-dimethyl-nonan-3-one

There total 1 articles about (4S,5R,6R,7S)-9-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-4,6-dimethyl-nonan-3-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:

: 69739-34-0
t-butyldimethylsiyl triflate

: 82849-05-6
(4S,5R,6S,7S)-9-Benzyloxy-5-hydroxy-7-methoxy-4,6-dimethyl-nonan-3-one

: 82864-88-8
(4S,5R,6R,7S)-9-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-4,6-dimethyl-nonan-3-one

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃;
DOI:10.1021/ja00384a063

Reference yield:

: 82864-88-8
(4S,5R,6R,7S)-9-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-4,6-dimethyl-nonan-3-one

: 82849-17-0
Trifluoro-acetic acid (1R,2R,3S)-3-methoxy-2-methyl-5-(toluene-4-sulfonyloxy)-1-((R)-1-{(4R,5R,6S)-2,2,5-trimethyl-6-[(S)-1-(5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-ethyl]-[1,3]dioxan-4-yl}-ethyl)-pentyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: lithium 1,1,3,3-tetramethyl-1,3-diphenyldisilazide, bis(cyclopentadienyl)zirconium dichloride / tetrahydrofuran / -40 deg C -> -20 deg C

2: diisobutylaluminium hydride / diethyl ether / -78 °C

3: conc. H₂SO₄ / acetone / 0 °C

4: n-Bu₄NF / tetrahydrofuran / 36 h / 40 °C

5: imidazole / tetrahydrofuran

6: Collins-Ratcliffe oxidation

7: tetrahydrofuran / -78 °C

8: 1.) NaBH₄, 2.) hydrogen / 2.) 5percent Pd/C

9: triethylamine / benzene

10: hydrolysis

11: C₅H₅N / CH₂Cl₂ / 48 h / 0 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; zirconocene dichloride; lithium bis(dimethylphenylsilyl)amide; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; benzene;
DOI:10.1021/ja00384a063

Reference yield:

: 82864-88-8
(4S,5R,6R,7S)-9-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-4,6-dimethyl-nonan-3-one

: 82849-10-3
(2S,3R,4S,5S)-7-Benzyloxy-2-[(4S,5R,6S)-6-((S)-2-hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-5-methoxy-4-methyl-heptan-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1: lithium 1,1,3,3-tetramethyl-1,3-diphenyldisilazide, bis(cyclopentadienyl)zirconium dichloride / tetrahydrofuran / -40 deg C -> -20 deg C

2: diisobutylaluminium hydride / diethyl ether / -78 °C

3: conc. H₂SO₄ / acetone / 0 °C

4: n-Bu₄NF / tetrahydrofuran / 36 h / 40 °C

With zirconocene dichloride; lithium bis(dimethylphenylsilyl)amide; sulfuric acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; acetone;
DOI:10.1021/ja00384a063