4-Benzyloxy-3-bromo-1-((2S,3R)-3-hydroxy-tetrahydro-pyran-2-yl)-butan-2-one

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Chemical Name:4-Benzyloxy-3-bromo-1-((2S,3R)-3-hydroxy-tetrahydro-pyran-2-yl)-butan-2-one
CAS No.:693239-40-6
Molecular Formula:C₁₆H₂₁BrO₄
Molecular Weight:357.244
Hs Code.:

Synonyms:4-Benzyloxy-3-bromo-1-((2S,3R)-3-hydroxy-tetrahydro-pyran-2-yl)-butan-2-one

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Chemical Property of 4-Benzyloxy-3-bromo-1-((2S,3R)-3-hydroxy-tetrahydro-pyran-2-yl)-butan-2-one

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Technology Process of 4-Benzyloxy-3-bromo-1-((2S,3R)-3-hydroxy-tetrahydro-pyran-2-yl)-butan-2-one

There total 6 articles about 4-Benzyloxy-3-bromo-1-((2S,3R)-3-hydroxy-tetrahydro-pyran-2-yl)-butan-2-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: 83.0%

: 693239-39-3
(2S,3R)-2-[3-Benzyloxymethyl-2-(toluene-4-sulfonyl)-oxiranylmethyl]-tetrahydro-pyran-3-ol

: 693239-40-6
4-Benzyloxy-3-bromo-1-((2S,3R)-3-hydroxy-tetrahydro-pyran-2-yl)-butan-2-one

Guidance literature:: With magnesium bromide ethyl etherate; In dichloromethane; at 20 ℃; for 1.5h;
DOI:10.1021/ol049569l

Reference yield:

: 121422-51-3
(2S,3R)-3-hydroxy-2-vinyloxane

: 693239-40-6
4-Benzyloxy-3-bromo-1-((2S,3R)-3-hydroxy-tetrahydro-pyran-2-yl)-butan-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: imidazole; 4-dimethylaminopyridine / dimethylformamide / 20 °C

2.1: OsO₄; 4-methylmorpholine N-oxide / tetrahydrofuran; H₂O / 20 °C

2.2: NaIO₄

2.3: NaBH₄ / methanol / 0 °C

3.1: 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

4.1: 15.01 g / HMPA; n-BuLi / tetrahydrofuran; hexane / 1 h / -100 °C

5.1: 62 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

6.1: 83 percent / magnesium bromide diethyl etherate / CH₂Cl₂ / 1.5 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; osmium(VIII) oxide; n-butyllithium; tetrabutyl ammonium fluoride; magnesium bromide ethyl etherate; 4-methylmorpholine N-oxide; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ol049569l

Reference yield:

: 262853-09-8
Trifluoro-methanesulfonic acid (2S,3R)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester

: 693239-40-6
4-Benzyloxy-3-bromo-1-((2S,3R)-3-hydroxy-tetrahydro-pyran-2-yl)-butan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: 15.01 g / HMPA; n-BuLi / tetrahydrofuran; hexane / 1 h / -100 °C

2: 62 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

3: 83 percent / magnesium bromide diethyl etherate / CH₂Cl₂ / 1.5 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; tetrabutyl ammonium fluoride; magnesium bromide ethyl etherate; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol049569l