(E)-(4S,5R,6R)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5,7,7-trimethyl-oct-2-enedioic acid diethyl ester

Base Information

Chemical Name:(E)-(4S,5R,6R)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5,7,7-trimethyl-oct-2-enedioic acid diethyl ester
CAS No.:297131-76-1
Molecular Formula:C₂₈H₄₆O₆Si
Molecular Weight:506.755
Hs Code.:

Synonyms:(E)-(4S,5R,6R)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5,7,7-trimethyl-oct-2-enedioic acid diethyl ester

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Chemical Property of (E)-(4S,5R,6R)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5,7,7-trimethyl-oct-2-enedioic acid diethyl ester

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Technology Process of (E)-(4S,5R,6R)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5,7,7-trimethyl-oct-2-enedioic acid diethyl ester

There total 8 articles about (E)-(4S,5R,6R)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5,7,7-trimethyl-oct-2-enedioic acid diethyl 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:

: 14642-79-6
benzyloxy-trimethylsilane

: 297131-76-1
(E)-(4S,5R,6R)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5,7,7-trimethyl-oct-2-enedioic acid diethyl ester

Guidance literature:: Multi-step reaction with 8 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

8.1: benzene / 4 h / Heating

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; benzene; 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

: 297131-76-1
(E)-(4S,5R,6R)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5,7,7-trimethyl-oct-2-enedioic acid diethyl ester

Guidance literature:: Multi-step reaction with 5 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

5: benzene / 4 h / Heating

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

Reference yield:

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

: 297131-76-1
(E)-(4S,5R,6R)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5,7,7-trimethyl-oct-2-enedioic acid diethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2: benzene / 4 h / Heating

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; benzene; 1: Swern oxidation;
DOI:10.1002/1099-0690(200105)2001:9<1701::AID-EJOC1701>3.0.CO;2-#