(3aS,6R,7aR,7R)-(5-benzyl-7-benzyloxy-2,2-dimethyl-hexahydro-1,3-dioxolo[4,5-c]pyridin-6-yl)methanol

Base Information

Chemical Name:(3aS,6R,7aR,7R)-(5-benzyl-7-benzyloxy-2,2-dimethyl-hexahydro-1,3-dioxolo[4,5-c]pyridin-6-yl)methanol
CAS No.:531515-09-0
Molecular Formula:C₂₃H₂₉NO₄
Molecular Weight:383.488
Hs Code.:

Synonyms:(3aS,6R,7aR,7R)-(5-benzyl-7-benzyloxy-2,2-dimethyl-hexahydro-1,3-dioxolo[4,5-c]pyridin-6-yl)methanol

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Chemical Property of (3aS,6R,7aR,7R)-(5-benzyl-7-benzyloxy-2,2-dimethyl-hexahydro-1,3-dioxolo[4,5-c]pyridin-6-yl)methanol

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Technology Process of (3aS,6R,7aR,7R)-(5-benzyl-7-benzyloxy-2,2-dimethyl-hexahydro-1,3-dioxolo[4,5-c]pyridin-6-yl)methanol

There total 13 articles about (3aS,6R,7aR,7R)-(5-benzyl-7-benzyloxy-2,2-dimethyl-hexahydro-1,3-dioxolo[4,5-c]pyridin-6-yl)methanol 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: 100.0%

: 531515-08-9
(3aS,6R,7aR,7R)-5-benzyl-7-benzyloxy-6-(tert-butyldiphenylsilanyloxymethyl)-2,2-dimethyl-hexahydro-1,3-dioxolo[4,5-c]pyridine

: 531515-09-0
(3aS,6R,7aR,7R)-(5-benzyl-7-benzyloxy-2,2-dimethyl-hexahydro-1,3-dioxolo[4,5-c]pyridin-6-yl)methanol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 14h;
DOI:10.1016/S0040-4020(02)01660-5

Reference yield:

: 531515-01-2
(E)-ethyl (4S,5S)-4,5-dihydroxy-6-(4-methoxybenzyloxy)-hex-2-enoate

: 531515-09-0
(3aS,6R,7aR,7R)-(5-benzyl-7-benzyloxy-2,2-dimethyl-hexahydro-1,3-dioxolo[4,5-c]pyridin-6-yl)methanol

Guidance literature:: Multi-step reaction with 12 steps

1: 97 percent / p-toluenesulfonic acid / dimethylformamide

2: 93 percent / diisobutylaluminum hydride / CH₂Cl₂ / 0.5 h / -78 °C

3: 80 percent / Ti(Oi-Pr)4; (+)-diisopropyl tartrate; t-BuOOH / CH₂Cl₂ / -20 °C

4: 97 percent / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 16 h / 20 °C

5: 92 percent / 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile / CH₂Cl₂; H₂O / 3 h / 20 °C

6: 100 percent / diisopropylethylamine / CH₂Cl₂ / 20 °C

7: 91 percent / NaN₃ / dimethylformamide / 80 °C

8: 83 percent / triphenylphosphine / tetrahydrofuran; H₂O / 20 °C

9: 90 percent / ethanol / 65 h / Heating

10: 82 percent / potassium bis(trimethylsilyl)amide / tetrahydrofuran / 2 h / -78 °C

11: 97 percent / potassium carbonate / acetonitrile / 5 h / Heating

12: 100 percent / tetra-n-butylammonium fluoride dihydrate / tetrahydrofuran / 14 h / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium azide; L-(+)-diisopropyl tartrate; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4020(02)01660-5

Reference yield:

: (2E,4E)-6-(4-Methoxy-benzyloxy)-hexa-2,4-dienoic acid ethyl ester

: 531515-09-0
(3aS,6R,7aR,7R)-(5-benzyl-7-benzyloxy-2,2-dimethyl-hexahydro-1,3-dioxolo[4,5-c]pyridin-6-yl)methanol

Guidance literature:: Multi-step reaction with 13 steps

1: 80 percent / AD-mix-α; K2OsO4*2H2O; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 46 h / 0 °C

2: 97 percent / p-toluenesulfonic acid / dimethylformamide

3: 93 percent / diisobutylaluminum hydride / CH₂Cl₂ / 0.5 h / -78 °C

4: 80 percent / Ti(Oi-Pr)4; (+)-diisopropyl tartrate; t-BuOOH / CH₂Cl₂ / -20 °C

5: 97 percent / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 16 h / 20 °C

6: 92 percent / 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile / CH₂Cl₂; H₂O / 3 h / 20 °C

7: 100 percent / diisopropylethylamine / CH₂Cl₂ / 20 °C

8: 91 percent / NaN₃ / dimethylformamide / 80 °C

9: 83 percent / triphenylphosphine / tetrahydrofuran; H₂O / 20 °C

10: 90 percent / ethanol / 65 h / Heating

11: 82 percent / potassium bis(trimethylsilyl)amide / tetrahydrofuran / 2 h / -78 °C

12: 97 percent / potassium carbonate / acetonitrile / 5 h / Heating

13: 100 percent / tetra-n-butylammonium fluoride dihydrate / tetrahydrofuran / 14 h / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; potassium osmate(VI); AD-mix-α; sodium azide; L-(+)-diisopropyl tartrate; methanesulfonamide; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
DOI:10.1016/S0040-4020(02)01660-5