(3aR,5S,9aR,9bS)-5-(1-hydroxycyclohexyl)-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c][1,3]oxazolo[3,4-a]pyridin-7-one

Base Information

Chemical Name:(3aR,5S,9aR,9bS)-5-(1-hydroxycyclohexyl)-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c][1,3]oxazolo[3,4-a]pyridin-7-one
CAS No.:1416449-42-7
Molecular Formula:C₁₆H₂₅NO₅
Molecular Weight:311.378
Hs Code.:

Synonyms:(3aR,5S,9aR,9bS)-5-(1-hydroxycyclohexyl)-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c][1,3]oxazolo[3,4-a]pyridin-7-one

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Chemical Property of (3aR,5S,9aR,9bS)-5-(1-hydroxycyclohexyl)-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c][1,3]oxazolo[3,4-a]pyridin-7-one

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Technology Process of (3aR,5S,9aR,9bS)-5-(1-hydroxycyclohexyl)-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c][1,3]oxazolo[3,4-a]pyridin-7-one

There total 8 articles about (3aR,5S,9aR,9bS)-5-(1-hydroxycyclohexyl)-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c][1,3]oxazolo[3,4-a]pyridin-7-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: 80.0%

: 1416449-29-0
(5S,8aS)-5-(1-hydroxycyclohexyl)-1,5,6,8a-tetrahydro[1,3]oxazolo[3,4-a]pyridin-3-one

: 77-76-9
2,2-dimethoxy-propane

: 1416449-41-6
(3aS,5S,9aR,9bR)-5-(1-hydroxycyclohexyl)-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c][1,3]oxazolo[3,4-a]pyridin-7-one

: 1416449-42-7
(3aR,5S,9aR,9bS)-5-(1-hydroxycyclohexyl)-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c][1,3]oxazolo[3,4-a]pyridin-7-one

Guidance literature:: (5S,8aS)-5-(1-hydroxycyclohexyl)-1,5,6,8a-tetrahydro[1,3]oxazolo[3,4-a]pyridin-3-one; With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; tert-butyl alcohol; at 20 ℃;

2,2-dimethoxy-propane; With camphor-10-sulfonic acid; In acetone; at 20 ℃; for 12h; Overall yield = 94 %; diastereoselective reaction;
DOI:10.1021/ol303213r

Reference yield:

: C₁₃H₂₁NO₅

: 77-76-9
2,2-dimethoxy-propane

: 1416449-41-6
(3aS,5S,9aR,9bR)-5-(1-hydroxycyclohexyl)-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c][1,3]oxazolo[3,4-a]pyridin-7-one

: 1416449-42-7
(3aR,5S,9aR,9bS)-5-(1-hydroxycyclohexyl)-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c][1,3]oxazolo[3,4-a]pyridin-7-one

Guidance literature:: With (R)-10-camphorsulfonic acid; In acetone; at 20 ℃; for 12h;
DOI:10.1039/d0ob02249g

Reference yield:

: 1416449-18-7,1416449-21-2
(4S)-3-[(1R)-1-tributylstannylbut-3-en-1-yl]-4-ethenyl-1,3-oxazolidin-2-one

: 1416449-41-6
(3aS,5S,9aR,9bR)-5-(1-hydroxycyclohexyl)-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c][1,3]oxazolo[3,4-a]pyridin-7-one

: 1416449-42-7
(3aR,5S,9aR,9bS)-5-(1-hydroxycyclohexyl)-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c][1,3]oxazolo[3,4-a]pyridin-7-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere; Schlenk technique

1.2: 0.33 h / -78 °C / Inert atmosphere; Schlenk technique

2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 40 °C

3.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / acetone; water; tert-butyl alcohol / 20 °C

3.2: 12 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; osmium(VIII) oxide; n-butyllithium; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; water; acetone; tert-butyl alcohol;
DOI:10.1021/ol303213r