(3R,4R,5S,6S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,2,4,6-tetramethyl-octanedioic acid diethyl ester

Base Information

Chemical Name:(3R,4R,5S,6S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,2,4,6-tetramethyl-octanedioic acid diethyl ester
CAS No.:297131-77-2
Molecular Formula:C₂₉H₅₀O₆Si
Molecular Weight:522.798
Hs Code.:

Synonyms:(3R,4R,5S,6S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,2,4,6-tetramethyl-octanedioic acid diethyl ester

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Chemical Property of (3R,4R,5S,6S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,2,4,6-tetramethyl-octanedioic acid diethyl ester

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Technology Process of (3R,4R,5S,6S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,2,4,6-tetramethyl-octanedioic acid diethyl ester

There total 9 articles about (3R,4R,5S,6S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,2,4,6-tetramethyl-octanedioic 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: 94.0%

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

: 297131-77-2
(3R,4R,5S,6S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,2,4,6-tetramethyl-octanedioic acid diethyl ester

Guidance literature:: With chloro-trimethyl-silane; In tetrahydrofuran; at -78 ℃; for 4h;
DOI:10.1002/1099-0690(200105)2001:9<1701::AID-EJOC1701>3.0.CO;2-#

Reference yield:

: 14642-79-6
benzyloxy-trimethylsilane

: 297131-77-2
(3R,4R,5S,6S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,2,4,6-tetramethyl-octanedioic acid diethyl ester

Guidance literature:: Multi-step reaction with 9 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

9.1: 94 percent / trimethylsilyl chloride / tetrahydrofuran / 4 h / -78 °C

With pyridine; 2,6-dimethylpyridine; chloro-trimethyl-silane; 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

: 297131-77-2
(3R,4R,5S,6S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,2,4,6-tetramethyl-octanedioic acid diethyl ester

Guidance literature:: Multi-step reaction with 6 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

6: 94 percent / trimethylsilyl chloride / tetrahydrofuran / 4 h / -78 °C

With 2,6-dimethylpyridine; chloro-trimethyl-silane; 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-#