(3aS,6S,7aR,7R)-5-benzyl-7-benzyloxy-2,2-dimethyl-hexahydro-1,3-dioxolo[4,5-c]pyridine-6-carbaldehyde

Base Information

Chemical Name:(3aS,6S,7aR,7R)-5-benzyl-7-benzyloxy-2,2-dimethyl-hexahydro-1,3-dioxolo[4,5-c]pyridine-6-carbaldehyde
CAS No.:531515-10-3
Molecular Formula:C₂₃H₂₇NO₄
Molecular Weight:381.472
Hs Code.:

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

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

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

There total 14 articles about (3aS,6S,7aR,7R)-5-benzyl-7-benzyloxy-2,2-dimethyl-hexahydro-1,3-dioxolo[4,5-c]pyridine-6-carbaldehyde 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:

: 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

: 531515-10-3
(3aS,6S,7aR,7R)-5-benzyl-7-benzyloxy-2,2-dimethyl-hexahydro-1,3-dioxolo[4,5-c]pyridine-6-carbaldehyde

Guidance literature:: With oxalyl dichloride; triethylamine; In dichloromethane; dimethyl sulfoxide; at -78 - 20 ℃;
DOI:10.1016/S0040-4020(02)01660-5

Reference yield:

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

: 531515-10-3
(3aS,6S,7aR,7R)-5-benzyl-7-benzyloxy-2,2-dimethyl-hexahydro-1,3-dioxolo[4,5-c]pyridine-6-carbaldehyde

Guidance literature:: Multi-step reaction with 14 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

14: (COCl)2; triethylamine / dimethylsulfoxide; CH₂Cl₂ / -78 - 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; potassium osmate(VI); AD-mix-α; sodium azide; oxalyl dichloride; 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; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 14: Swern oxidation;
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

: 531515-10-3
(3aS,6S,7aR,7R)-5-benzyl-7-benzyloxy-2,2-dimethyl-hexahydro-1,3-dioxolo[4,5-c]pyridine-6-carbaldehyde

Guidance literature:: Multi-step reaction with 13 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

13: (COCl)2; triethylamine / dimethylsulfoxide; CH₂Cl₂ / -78 - 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium azide; oxalyl dichloride; 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; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 13: Swern oxidation;
DOI:10.1016/S0040-4020(02)01660-5