Trifluoro-methanesulfonic acid (3aR,6R,7R,7aR)-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl ester

Base Information

Chemical Name:Trifluoro-methanesulfonic acid (3aR,6R,7R,7aR)-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl ester
CAS No.:431881-21-9
Molecular Formula:C₁₇H₂₁F₃O₇S
Molecular Weight:426.411
Hs Code.:

Synonyms:Trifluoro-methanesulfonic acid (3aR,6R,7R,7aR)-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl ester

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Chemical Property of Trifluoro-methanesulfonic acid (3aR,6R,7R,7aR)-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl ester

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Technology Process of Trifluoro-methanesulfonic acid (3aR,6R,7R,7aR)-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl ester

There total 5 articles about Trifluoro-methanesulfonic acid (3aR,6R,7R,7aR)-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl ester 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:

: 358-23-6
trifluoromethylsulfonic anhydride

: 431881-20-8
[(3aR,6R,7R,7aR)-7-(benzyloxy)-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl]methanol

: 431881-21-9
Trifluoro-methanesulfonic acid (3aR,6R,7R,7aR)-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl ester

Guidance literature:: With 2,6-di-tert-butyl-4-methylpyridine; In dichloromethane; at -55 - 20 ℃;
DOI:10.1021/jo0107610

Reference yield:

: 492-93-3,53319-04-3
1,5-anhydro-D-mannitol

: 431881-21-9
Trifluoro-methanesulfonic acid (3aR,6R,7R,7aR)-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: imidazole / dimethylformamide / 3 h / 0 °C

2.1: 16.9 g / CSA / dimethylformamide / 2 h

3.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

3.2: 15-crown-5 / tetrahydrofuran / 0 - 20 °C

4.1: 6.88 g / TBAF / tetrahydrofuran / 2 h

5.1: DTBMP / CH₂Cl₂ / -55 - 20 °C

With 1H-imidazole; 2,6-di-tert-butyl-4-methylpyridine; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo0107610

Reference yield:

: (2R,3S,4R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3,4,5-triol

: 431881-21-9
Trifluoro-methanesulfonic acid (3aR,6R,7R,7aR)-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 16.9 g / CSA / dimethylformamide / 2 h

2.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

2.2: 15-crown-5 / tetrahydrofuran / 0 - 20 °C

3.1: 6.88 g / TBAF / tetrahydrofuran / 2 h

4.1: DTBMP / CH₂Cl₂ / -55 - 20 °C

With 2,6-di-tert-butyl-4-methylpyridine; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo0107610