(2S,3aR,6S,6aS)-6-methyl-2-tosyloxymethyltetrahydrofuro[3,4-b]furan-4-one

Base Information

Chemical Name:(2S,3aR,6S,6aS)-6-methyl-2-tosyloxymethyltetrahydrofuro[3,4-b]furan-4-one
CAS No.:861902-84-3
Molecular Formula:C₁₅H₁₈O₆S
Molecular Weight:326.37
Hs Code.:

Synonyms:(2S,3aR,6S,6aS)-6-methyl-2-tosyloxymethyltetrahydrofuro[3,4-b]furan-4-one

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Chemical Property of (2S,3aR,6S,6aS)-6-methyl-2-tosyloxymethyltetrahydrofuro[3,4-b]furan-4-one

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Technology Process of (2S,3aR,6S,6aS)-6-methyl-2-tosyloxymethyltetrahydrofuro[3,4-b]furan-4-one

There total 8 articles about (2S,3aR,6S,6aS)-6-methyl-2-tosyloxymethyltetrahydrofuro[3,4-b]furan-4-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: 94.0%

: 98-59-9
p-toluenesulfonyl chloride

: 861902-83-2
(2S,3aR,6S,6aS)-2-hydroxymethyl-6-methyltetrahydrofuro[3,4-b]furan-4-one

: 861902-84-3
(2S,3aR,6S,6aS)-6-methyl-2-tosyloxymethyltetrahydrofuro[3,4-b]furan-4-one

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 2h;
DOI:10.1016/j.tet.2005.04.059

Reference yield:

: 861902-80-9
(1S,2'S,5'S)-1-[5'-(tert-butyldiphenylsilanyloxymethyl)-2',5'-dihydrofuran-2'-yl]ethanol

: 861902-84-3
(2S,3aR,6S,6aS)-6-methyl-2-tosyloxymethyltetrahydrofuro[3,4-b]furan-4-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: pyridine / CH₂Cl₂ / 2.5 h / 0 - 20 °C

1.2: 95 percent / triethylamine / CH₂Cl₂ / 1.5 h / 0 - 20 °C

2.1: 93 percent / n-tributyltin hydride; AIBN / toluene / 0.67 h / 100 °C

3.1: 89 percent / n-tetrabutylammonium fluoride / tetrahydrofuran / 20 °C

4.1: 94 percent / N,N-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 2 h / 0 - 20 °C

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; triethylamine; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1016/j.tet.2005.04.059

Reference yield:

: 861902-78-5
(1'S,2S,5S)-2-(1'-methoxymethoxyethyl)-5-trityloxymethyl-2,5-dihydrofuran

: 861902-84-3
(2S,3aR,6S,6aS)-6-methyl-2-tosyloxymethyltetrahydrofuro[3,4-b]furan-4-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 97 percent / hydrogen chloride / CH₂Cl₂; methanol / 48 h / 0 - 20 °C

2.1: 81 percent / imidazole / dimethylformamide / 6 h / 20 °C

3.1: pyridine / CH₂Cl₂ / 2.5 h / 0 - 20 °C

3.2: 95 percent / triethylamine / CH₂Cl₂ / 1.5 h / 0 - 20 °C

4.1: 93 percent / n-tributyltin hydride; AIBN / toluene / 0.67 h / 100 °C

5.1: 89 percent / n-tetrabutylammonium fluoride / tetrahydrofuran / 20 °C

6.1: 94 percent / N,N-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 2 h / 0 - 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tet.2005.04.059