(3aR,6S,7S,7aR)-4-Methoxy-6-methyl-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol

Base Information

Chemical Name:(3aR,6S,7S,7aR)-4-Methoxy-6-methyl-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol
CAS No.:795289-91-7
Molecular Formula:C₁₄H₁₈O₅
Molecular Weight:266.294
Hs Code.:

Synonyms:(3aR,6S,7S,7aR)-4-Methoxy-6-methyl-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol

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Chemical Property of (3aR,6S,7S,7aR)-4-Methoxy-6-methyl-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol

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Technology Process of (3aR,6S,7S,7aR)-4-Methoxy-6-methyl-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol

There total 1 articles about (3aR,6S,7S,7aR)-4-Methoxy-6-methyl-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-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:

: 1125-88-8
benzaldehyde dimethyl acetal

: 1128-40-1,1198-82-9,2592-55-4,5155-43-1,6340-52-9,10503-91-0,14009-07-5,14687-15-1,14917-55-6,15814-59-2,24332-98-7,34299-65-5,42214-00-6,42214-11-9,57783-34-3,57783-36-5,57783-38-7,57783-40-1,57783-42-3,58525-46-5,58525-47-6,58525-48-7,62182-01-8,62182-02-9,65310-00-1,65941-62-0,68069-80-7,71116-57-9,72274-54-5,72274-55-6,73036-22-3,83198-64-5,85505-15-3,102517-74-8,109718-80-1,109718-81-2,125280-09-3,129172-95-8,63864-94-8
methyl L-rhamnopyranoside

: 795289-91-7
(3aR,6S,7S,7aR)-4-Methoxy-6-methyl-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol

Guidance literature:: With toluene-4-sulfonic acid; In N,N-dimethyl-formamide;
DOI:10.1002/anie.200460172 DOI:10.1002/chem.200600462

Reference yield:

: 795289-91-7
(3aR,6S,7S,7aR)-4-Methoxy-6-methyl-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol

: (2S,3S,4S)-3-[(2R,3R,4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-iodomethyl-4-methoxy-3-phenylsulfanyl-tetrahydro-pyran-2-yloxy]-2,4-dimethyl-4-triethylsilanyloxy-3,4-dihydro-2H-pyran

Guidance literature:: Multi-step reaction with 6 steps

1: 43 percent / tetrahydrofuran / 30 h / 20 °C

2: 4-dimethylaminopyridine / CH₂Cl₂

3: lutidine

4: diisobutylaluminum hydride / CH₂Cl₂ / -60 °C

5: TMSOTf / diethyl ether / 1 h / -60 - -40 °C

6: NaI / dimethylformamide / 2 h / 90 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; lutidine; diisobutylaluminium hydride; sodium iodide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/anie.200460172

Reference yield:

: 795289-91-7
(3aR,6S,7S,7aR)-4-Methoxy-6-methyl-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol

: 795289-96-2
Toluene-4-sulfonic acid (2R,3R,4S,5R,6S)-3-(tert-butyl-dimethyl-silanyloxy)-6-((2S,3S,4S)-2,4-dimethyl-4-triethylsilanyloxy-3,4-dihydro-2H-pyran-3-yloxy)-4-methoxy-5-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 43 percent / tetrahydrofuran / 30 h / 20 °C

2: 4-dimethylaminopyridine / CH₂Cl₂

3: lutidine

4: diisobutylaluminum hydride / CH₂Cl₂ / -60 °C

5: TMSOTf / diethyl ether / 1 h / -60 - -40 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; lutidine; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1002/anie.200460172