(1S,2R,3S,4R,5R,7S)-3-Benzyloxy-7-hydroxymethyl-5-propyl-2-triethylsilanyloxy-4-triisopropylsilanyloxy-6-oxa-bicyclo[3.2.1]octan-8-one

Base Information

Chemical Name:(1S,2R,3S,4R,5R,7S)-3-Benzyloxy-7-hydroxymethyl-5-propyl-2-triethylsilanyloxy-4-triisopropylsilanyloxy-6-oxa-bicyclo[3.2.1]octan-8-one
CAS No.:871268-85-8
Molecular Formula:C₃₃H₅₈O₆Si₂
Molecular Weight:606.991
Hs Code.:

Synonyms:(1S,2R,3S,4R,5R,7S)-3-Benzyloxy-7-hydroxymethyl-5-propyl-2-triethylsilanyloxy-4-triisopropylsilanyloxy-6-oxa-bicyclo[3.2.1]octan-8-one

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Chemical Property of (1S,2R,3S,4R,5R,7S)-3-Benzyloxy-7-hydroxymethyl-5-propyl-2-triethylsilanyloxy-4-triisopropylsilanyloxy-6-oxa-bicyclo[3.2.1]octan-8-one

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Technology Process of (1S,2R,3S,4R,5R,7S)-3-Benzyloxy-7-hydroxymethyl-5-propyl-2-triethylsilanyloxy-4-triisopropylsilanyloxy-6-oxa-bicyclo[3.2.1]octan-8-one

There total 11 articles about (1S,2R,3S,4R,5R,7S)-3-Benzyloxy-7-hydroxymethyl-5-propyl-2-triethylsilanyloxy-4-triisopropylsilanyloxy-6-oxa-bicyclo[3.2.1]octan-8-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: 99.0%

: 871268-99-4
(1S,2R,3S,4R,5R,7S)-3-Benzyloxy-7-benzyloxymethyl-5-propyl-2-triethylsilanyloxy-4-triisopropylsilanyloxy-6-oxa-bicyclo[3.2.1]octan-8-one

: 871268-85-8
(1S,2R,3S,4R,5R,7S)-3-Benzyloxy-7-hydroxymethyl-5-propyl-2-triethylsilanyloxy-4-triisopropylsilanyloxy-6-oxa-bicyclo[3.2.1]octan-8-one

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 36h; under 760 Torr;
DOI:10.1021/ol052321r

Reference yield:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 871268-85-8
(1S,2R,3S,4R,5R,7S)-3-Benzyloxy-7-hydroxymethyl-5-propyl-2-triethylsilanyloxy-4-triisopropylsilanyloxy-6-oxa-bicyclo[3.2.1]octan-8-one

Guidance literature:: Multi-step reaction with 6 steps

1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

2: 81 percent / p-TsOH*H₂O / methanol / 0 - 20 °C

3: DMSO; oxalyl chloride; triethylamine / CH₂Cl₂ / -50 - 20 °C

4: 46 percent / Na₂CO₃*10H₂O / tetrahydrofuran; methanol; H₂O / 1 h / 20 °C

5: 97 percent / imidazole / CH₂Cl₂ / 0.5 h / 20 °C

6: 99 percent / H₂ / Pd/C / ethanol / 36 h / 20 °C / 760 Torr

With 1H-imidazole; 2,6-dimethylpyridine; oxalyl dichloride; hydrogen; sodium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 3: Swern oxidation;
DOI:10.1021/ol052321r

Reference yield:

: 871268-78-9
(2S,3S,5S)-2-((1R,2S)-2-Benzyloxy-3-hydroxy-1-triisopropylsilanyloxy-propyl)-5-benzyloxymethyl-2-propyl-tetrahydro-furan-3-ol

: 871268-85-8
(1S,2R,3S,4R,5R,7S)-3-Benzyloxy-7-hydroxymethyl-5-propyl-2-triethylsilanyloxy-4-triisopropylsilanyloxy-6-oxa-bicyclo[3.2.1]octan-8-one

Guidance literature:: Multi-step reaction with 4 steps

1: DMSO; oxalyl chloride; triethylamine / CH₂Cl₂ / -50 - 20 °C

2: 46 percent / Na₂CO₃*10H₂O / tetrahydrofuran; methanol; H₂O / 1 h / 20 °C

3: 97 percent / imidazole / CH₂Cl₂ / 0.5 h / 20 °C

4: 99 percent / H₂ / Pd/C / ethanol / 36 h / 20 °C / 760 Torr

With 1H-imidazole; oxalyl dichloride; hydrogen; sodium carbonate; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 1: Swern oxidation;
DOI:10.1021/ol052321r