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

Base Information

Chemical Name:(2S,3R)-2-[3-Benzyloxymethyl-2-(toluene-4-sulfonyl)-oxiranylmethyl]-tetrahydro-pyran-3-ol
CAS No.:693239-39-3
Molecular Formula:C₂₃H₂₈O₆S
Molecular Weight:432.538
Hs Code.:

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

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Chemical Property of (2S,3R)-2-[3-Benzyloxymethyl-2-(toluene-4-sulfonyl)-oxiranylmethyl]-tetrahydro-pyran-3-ol

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Technology Process of (2S,3R)-2-[3-Benzyloxymethyl-2-(toluene-4-sulfonyl)-oxiranylmethyl]-tetrahydro-pyran-3-ol

There total 5 articles about (2S,3R)-2-[3-Benzyloxymethyl-2-(toluene-4-sulfonyl)-oxiranylmethyl]-tetrahydro-pyran-3-ol 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: 62.0%

: 693239-38-2
{(2S,3R)-2-[3-Benzyloxymethyl-2-(toluene-4-sulfonyl)-oxiranylmethyl]-tetrahydro-pyran-3-yloxy}-tert-butyl-dimethyl-silane

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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1021/ol049569l

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 5 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

With 1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; osmium(VIII) oxide; n-butyllithium; tetrabutyl ammonium fluoride; 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

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

Guidance literature:: Multi-step reaction with 2 steps

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

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

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