(3S)-3-((3aS,6R,7aR,7R)-5-benzyl-7-benzyloxy-2,2-dimethylhexahydro-1,3-dioxolo[4,5-c]pyridin-6-yl)-3-hydroxypropionaldehyde

Base Information

Chemical Name:(3S)-3-((3aS,6R,7aR,7R)-5-benzyl-7-benzyloxy-2,2-dimethylhexahydro-1,3-dioxolo[4,5-c]pyridin-6-yl)-3-hydroxypropionaldehyde
CAS No.:531515-12-5
Molecular Formula:C₂₅H₃₁NO₅
Molecular Weight:425.525
Hs Code.:

Synonyms:

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

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

There total 17 articles about (3S)-3-((3aS,6R,7aR,7R)-5-benzyl-7-benzyloxy-2,2-dimethylhexahydro-1,3-dioxolo[4,5-c]pyridin-6-yl)-3-hydroxypropionaldehyde 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:

: 531515-14-7
(S)-4-((3aS,6R,7R,7aR)-5-Benzyl-7-benzyloxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-6-yl)-butane-1,2,4-triol

: 531515-12-5
(3S)-3-((3aS,6R,7aR,7R)-5-benzyl-7-benzyloxy-2,2-dimethylhexahydro-1,3-dioxolo[4,5-c]pyridin-6-yl)-3-hydroxypropionaldehyde

Guidance literature:: With sodium periodate; sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃; for 3h;
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

: 531515-12-5
(3S)-3-((3aS,6R,7aR,7R)-5-benzyl-7-benzyloxy-2,2-dimethylhexahydro-1,3-dioxolo[4,5-c]pyridin-6-yl)-3-hydroxypropionaldehyde

Guidance literature:: Multi-step reaction with 16 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

14: 71 percent / TiCl₄ / CH₂Cl₂ / 15 h / -78 °C

15: OsO₄; 4-methylmorpholine N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 3 h / 20 °C

16: 45 mg / NaHCO₃; NaIO₄ / tetrahydrofuran; H₂O / 3 h / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium periodate; osmium(VIII) oxide; sodium azide; oxalyl dichloride; L-(+)-diisopropyl tartrate; tetrabutyl ammonium fluoride; titanium tetrachloride; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 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; 13: Swern oxidation;
DOI:10.1016/S0040-4020(02)01660-5

Reference yield:

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

: 531515-12-5
(3S)-3-((3aS,6R,7aR,7R)-5-benzyl-7-benzyloxy-2,2-dimethylhexahydro-1,3-dioxolo[4,5-c]pyridin-6-yl)-3-hydroxypropionaldehyde

Guidance literature:: Multi-step reaction with 17 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

15: 71 percent / TiCl₄ / CH₂Cl₂ / 15 h / -78 °C

16: OsO₄; 4-methylmorpholine N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 3 h / 20 °C

17: 45 mg / NaHCO₃; NaIO₄ / tetrahydrofuran; H₂O / 3 h / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; potassium osmate(VI); sodium periodate; AD-mix-α; osmium(VIII) oxide; sodium azide; oxalyl dichloride; L-(+)-diisopropyl tartrate; methanesulfonamide; tetrabutyl ammonium fluoride; titanium tetrachloride; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 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