(3R,4R,5R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,2,4-trimethyl-6-oxo-hexanoic acid ethyl ester

Base Information

Chemical Name:(3R,4R,5R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,2,4-trimethyl-6-oxo-hexanoic acid ethyl ester
CAS No.:297131-89-6
Molecular Formula:C₂₄H₄₀O₅Si
Molecular Weight:436.664
Hs Code.:

Synonyms:(3R,4R,5R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,2,4-trimethyl-6-oxo-hexanoic acid ethyl ester

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Chemical Property of (3R,4R,5R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,2,4-trimethyl-6-oxo-hexanoic acid ethyl ester

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Technology Process of (3R,4R,5R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,2,4-trimethyl-6-oxo-hexanoic acid ethyl ester

There total 7 articles about (3R,4R,5R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,2,4-trimethyl-6-oxo-hexanoic acid ethyl ester 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: 95.0%

: 297131-75-0
(3R,4R,5R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-2,2,4-trimethyl-hexanoic acid ethyl ester

: 297131-89-6
(3R,4R,5R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,2,4-trimethyl-6-oxo-hexanoic acid ethyl ester

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;
DOI:10.1021/ol006104w

Reference yield:

: 14642-79-6
benzyloxy-trimethylsilane

: 297131-89-6
(3R,4R,5R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,2,4-trimethyl-6-oxo-hexanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 16 h / -78 - -50 °C

2.1: BF₃*Et₂O / CH₂Cl₂ / 24 h / -30 °C

3.1: O₃; pyridine / methanol; CH₂Cl₂ / 0.5 h / -78 °C

3.2: 88 percent / dimethylsulfide / pyridine; methanol; CH₂Cl₂ / 16 h / 20 °C

4.1: TiCl₄ / CH₂Cl₂ / 0.75 h / -78 °C

5.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

6.1: 92 percent / tetrabutylammonium fluoride; acetic acid / tetrahydrofuran / 24 h / 20 °C

7.1: 95 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

With pyridine; 2,6-dimethylpyridine; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; titanium tetrachloride; ozone; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 7.1: Swern oxidation;
DOI:10.1002/1099-0690(200105)2001:9<1701::AID-EJOC1701>3.0.CO;2-#

Reference yield:

: 297131-87-4
(2R,3R)-3-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-2-methyl-butyraldehyde

: 297131-89-6
(3R,4R,5R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,2,4-trimethyl-6-oxo-hexanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: TiCl₄ / CH₂Cl₂ / 0.75 h / -78 °C

2: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

3: 92 percent / tetrabutylammonium fluoride; acetic acid / tetrahydrofuran / 24 h / 20 °C

4: 95 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

With 2,6-dimethylpyridine; oxalyl dichloride; tetrabutyl ammonium fluoride; titanium tetrachloride; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 4: Swern oxidation;
DOI:10.1002/1099-0690(200105)2001:9<1701::AID-EJOC1701>3.0.CO;2-#