(3R,3aR,5S,6S,7S,7aS)-7-Benzyloxy-5-methoxy-3,6-dimethyl-hexahydro-furo[3,2-b]pyran-2-one

Base Information

Chemical Name:(3R,3aR,5S,6S,7S,7aS)-7-Benzyloxy-5-methoxy-3,6-dimethyl-hexahydro-furo[3,2-b]pyran-2-one
CAS No.:157219-94-8
Molecular Formula:C₁₇H₂₂O₅
Molecular Weight:306.359
Hs Code.:

Synonyms:(3R,3aR,5S,6S,7S,7aS)-7-Benzyloxy-5-methoxy-3,6-dimethyl-hexahydro-furo[3,2-b]pyran-2-one

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Chemical Property of (3R,3aR,5S,6S,7S,7aS)-7-Benzyloxy-5-methoxy-3,6-dimethyl-hexahydro-furo[3,2-b]pyran-2-one

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Technology Process of (3R,3aR,5S,6S,7S,7aS)-7-Benzyloxy-5-methoxy-3,6-dimethyl-hexahydro-furo[3,2-b]pyran-2-one

There total 14 articles about (3R,3aR,5S,6S,7S,7aS)-7-Benzyloxy-5-methoxy-3,6-dimethyl-hexahydro-furo[3,2-b]pyran-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:

: 259258-16-7
(3S,3aR,5S,6S,7S,7aS)-7-Benzyloxy-5-methoxy-3,6-dimethyl-hexahydro-furo[3,2-b]pyran-2-one

: 157219-94-8
(3R,3aR,5S,6S,7S,7aS)-7-Benzyloxy-5-methoxy-3,6-dimethyl-hexahydro-furo[3,2-b]pyran-2-one

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h;
DOI:10.1021/jo990988j

Reference yield:

: 109958-35-2
(2R,4aR,6S,7S,8S,8aS)-8-Benzyloxy-6-methoxy-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

: 157219-94-8
(3R,3aR,5S,6S,7S,7aS)-7-Benzyloxy-5-methoxy-3,6-dimethyl-hexahydro-furo[3,2-b]pyran-2-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 98 percent / p-toluenesulfonic acid monohydrate / methanol / 1.5 h / 20 °C

2.1: 47.10 g / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 4 h / 0 °C

3.1: 70 percent / dimethylsulfoxide / 1.5 h / 70 °C

4.1: DIBALH / CH₂Cl₂; hexane / 1 h / -78 °C

4.2: 12.38 g / HCl / CH₂Cl₂; hexane; H₂O / 0.25 h

5.1: 14.79 g / 2-methyl-2-butene; NaH₂PO₄*H₂O; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 0.33 h / 20 °C

6.1: 8.03 g / triethylamine; phenylsulfonyl chloride / CH₂Cl₂ / 0 - 20 °C

7.1: LiHMDS / tetrahydrofuran; hexane / 0.5 h / -78 °C

7.2: tetrahydrofuran; hexane / 0.5 h / -78 °C

8.1: 23.46 g / lithium diisopropylamide / tetrahydrofuran; hexane / 0.33 h / -78 °C

With dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; benzenesulfonyl chloride; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; tert-butyl alcohol; 1.1: Hydrolysis / 2.1: Tosylation / 3.1: Substitution / 4.1: Reduction / 4.2: Hydrolysis / 5.1: Oxidation / 6.1: Cyclization / 7.1: Metallation / 7.2: Methylation / 8.1: Metallation;
DOI:10.1021/jo990988j

Reference yield:

: 68907-47-1
methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-altro-pyranoside

: 157219-94-8
(3R,3aR,5S,6S,7S,7aS)-7-Benzyloxy-5-methoxy-3,6-dimethyl-hexahydro-furo[3,2-b]pyran-2-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: 99 percent / tetra-n-butylammonium iodide; sodium hydride / tetrahydrofuran; dimethylformamide; various solvent(s) / 20 °C

2.1: 98 percent / p-toluenesulfonic acid monohydrate / methanol / 1.5 h / 20 °C

3.1: 47.10 g / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 4 h / 0 °C

4.1: 70 percent / dimethylsulfoxide / 1.5 h / 70 °C

5.1: DIBALH / CH₂Cl₂; hexane / 1 h / -78 °C

5.2: 12.38 g / HCl / CH₂Cl₂; hexane; H₂O / 0.25 h

6.1: 14.79 g / 2-methyl-2-butene; NaH₂PO₄*H₂O; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 0.33 h / 20 °C

7.1: 8.03 g / triethylamine; phenylsulfonyl chloride / CH₂Cl₂ / 0 - 20 °C

8.1: LiHMDS / tetrahydrofuran; hexane / 0.5 h / -78 °C

8.2: tetrahydrofuran; hexane / 0.5 h / -78 °C

9.1: 23.46 g / lithium diisopropylamide / tetrahydrofuran; hexane / 0.33 h / -78 °C

With dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; benzenesulfonyl chloride; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Alkylation / 2.1: Hydrolysis / 3.1: Tosylation / 4.1: Substitution / 5.1: Reduction / 5.2: Hydrolysis / 6.1: Oxidation / 7.1: Cyclization / 8.1: Metallation / 8.2: Methylation / 9.1: Metallation;
DOI:10.1021/jo990988j