(2S,3S)-(-)-2-benzyloxy-3,4-epoxy-1-(tert-butyldimethyldimethylsiloxy)butane

Base Information

Chemical Name:(2S,3S)-(-)-2-benzyloxy-3,4-epoxy-1-(tert-butyldimethyldimethylsiloxy)butane
CAS No.:362675-40-9
Molecular Formula:C₁₇H₂₈O₃Si
Molecular Weight:308.493
Hs Code.:

Synonyms:(2S,3S)-(-)-2-benzyloxy-3,4-epoxy-1-(tert-butyldimethyldimethylsiloxy)butane

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Chemical Property of (2S,3S)-(-)-2-benzyloxy-3,4-epoxy-1-(tert-butyldimethyldimethylsiloxy)butane

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Technology Process of (2S,3S)-(-)-2-benzyloxy-3,4-epoxy-1-(tert-butyldimethyldimethylsiloxy)butane

There total 1 articles about (2S,3S)-(-)-2-benzyloxy-3,4-epoxy-1-(tert-butyldimethyldimethylsiloxy)butane 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: 63.0%

: 98-59-9
p-toluenesulfonyl chloride

: (2S,3S)-3-benzyloxy-4-[tert-butyl(dimethyl)silyloxy]butane-1,2-diol

: 362675-40-9
(2S,3S)-(-)-2-benzyloxy-3,4-epoxy-1-(tert-butyldimethyldimethylsiloxy)butane

Guidance literature:: p-toluenesulfonyl chloride; (2S,3S)-3-benzyloxy-4-[tert-butyl(dimethyl)silyloxy]butane-1,2-diol; In pyridine; for 8h;

With potassium carbonate; In methanol; for 1h; Further stages.;
DOI:10.1021/jo0104532

Reference yield:

: 362675-40-9
(2S,3S)-(-)-2-benzyloxy-3,4-epoxy-1-(tert-butyldimethyldimethylsiloxy)butane

: (2S,3S)-2-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-hexane-1,6-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-BuLi; BF₃*Et₂O / tetrahydrofuran / 0.08 h / -78 °C

2.1: imidazole / dimethylformamide / 4.5 h / 20 °C

2.2: K₂CO₃ / methanol / 1 h

3.1: 2.44 g / H₂; pyridine / Pd/Ba₂CO₃ / ethyl acetate / 4.5 h / 20 °C

4.1: BH₃*THF / tetrahydrofuran / 1 h / 20 °C

4.2: aq. NaOH; aq. H₂O₂ / tetrahydrofuran; H₂O / 1 h / 20 °C

With pyridine; 1H-imidazole; n-butyllithium; borane-THF; boron trifluoride diethyl etherate; hydrogen; palladium; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo0104532

Reference yield:

: 362675-40-9
(2S,3S)-(-)-2-benzyloxy-3,4-epoxy-1-(tert-butyldimethyldimethylsiloxy)butane

: 2,2-Dimethyl-propionic acid (4S,5R)-5-benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-hexyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-BuLi; BF₃*Et₂O / tetrahydrofuran / 0.08 h / -78 °C

2.1: imidazole / dimethylformamide / 4.5 h / 20 °C

2.2: K₂CO₃ / methanol / 1 h

3.1: 2.44 g / H₂; pyridine / Pd/Ba₂CO₃ / ethyl acetate / 4.5 h / 20 °C

4.1: BH₃*THF / tetrahydrofuran / 1 h / 20 °C

4.2: aq. NaOH; aq. H₂O₂ / tetrahydrofuran; H₂O / 1 h / 20 °C

5.1: Et₃N; dimethylaminopyridine / CH₂Cl₂ / 4 h / 20 °C

5.2: 426 mg / pyridinium p-toluenesulfonate / methanol / 24 h / 20 °C

6.1: DMSO; oxalyl chloride / CH₂Cl₂ / 1 h / -78 °C

6.2: triethylamine / CH₂Cl₂ / -78 - 20 °C

With pyridine; 1H-imidazole; dmap; n-butyllithium; borane-THF; oxalyl dichloride; boron trifluoride diethyl etherate; hydrogen; dimethyl sulfoxide; triethylamine; palladium; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 6.1: Swern oxidation;
DOI:10.1021/jo0104532