(3aR,5aR,8aR,8bS)-2,2,7-trimethyl-4-cyclohexyl-3a,5a,8a,8b-tetrahydro[1,3]dioxolo[4,5-e][1,3]benzoxazole

Base Information

• Chemical Name: (3aR,5aR,8aR,8bS)-2,2,7-trimethyl-4-cyclohexyl-3a,5a,8a,8b-tetrahydro[1,3]dioxolo[4,5-e][1,3]benzoxazole
• CAS No.: 1229922-79-5
• Molecular Formula: C₁₇H₂₅NO₃
• Molecular Weight: 291.39

Synonyms:(3aR,5aR,8aR,8bS)-2,2,7-trimethyl-4-cyclohexyl-3a,5a,8a,8b-tetrahydro[1,3]dioxolo[4,5-e][1,3]benzoxazole

Chemical Property of (3aR,5aR,8aR,8bS)-2,2,7-trimethyl-4-cyclohexyl-3a,5a,8a,8b-tetrahydro[1,3]dioxolo[4,5-e][1,3]benzoxazole

Chemical Property:

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Technology Process of (3aR,5aR,8aR,8bS)-2,2,7-trimethyl-4-cyclohexyl-3a,5a,8a,8b-tetrahydro[1,3]dioxolo[4,5-e][1,3]benzoxazole

There total 5 articles about (3aR,5aR,8aR,8bS)-2,2,7-trimethyl-4-cyclohexyl-3a,5a,8a,8b-tetrahydro[1,3]dioxolo[4,5-e][1,3]benzoxazole 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: 68.0%

(1S,2S,3S,6R)-6-acetylamino-1,2-O-isopropylidene-3-cyclohexylcyclohex-4-ene-1,2,3-triol (1229922-77-3) → (3aR,5aR,8aR,8bS)-2,2,7-trimethyl-4-cyclohexyl-3a,5a,8a,8b-tetrahydro[1,3]dioxolo[4,5-e][1,3]benzoxazole (1229922-79-5)

Guidance literature:

With triethylamine; Methanesulfonic anhydride; In 1,2-dichloro-ethane; at 4 - 15 ℃; stereoselective reaction;

DOI:10.1016/j.tet.2010.03.059

Reference yield: 32.0%

(1S,2S,3S,6R)-6-acetylamino-1,2-O-isopropylidene-3-cyclohexylcyclohex-4-ene-1,2,3-triol (1229922-77-3) → (3aR,5aR,8aR,8bS)-2,2,7-trimethyl-4-cyclohexyl-3a,5a,8a,8b-tetrahydro[1,3]dioxolo[4,5-e][1,3]benzoxazole (1229922-79-5) + (1S,2R,5R,6S)-6-acetylamino-1,2-O-isopropylidene-5-chloro-3-cyclohexylcyclohex-3-ene-1,2-diol (1229922-80-8)

Guidance literature:

With methanesulfonyl chloride; triethylamine; In 1,2-dichloro-ethane; at 4 - 60 ℃;

DOI:10.1016/j.tet.2010.03.059

Reference yield:

(3aS,4R,5S,7aR)-4-acetamido-7-cyclohexyl-N,N,N-triethyl-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo[d][1,3]dioxol-5-ammonium methanesulfonate → (3aR,5aR,8aR,8bS)-2,2,7-trimethyl-4-cyclohexyl-3a,5a,8a,8b-tetrahydro[1,3]dioxolo[4,5-e][1,3]benzoxazole (1229922-79-5)

Guidance literature:

With sodium hydrogencarbonate; In ethanol; at 80 ℃;

DOI:10.1016/j.tet.2010.03.059

upstream raw materials:

(1S,2R,5R,6S)-6-acetylamino-1,2-O-isopropylidene-5-chloro-3-cyclohexylcyclohex-3-ene-1,2-diol

(1S,2S,3S,6R)-6-acetylamino-1,2-O-isopropylidene-3-cyclohexylcyclohex-4-ene-1,2,3-triol

(1S,2R,5S,6S)-6-acetylamino-1,2-O-isopropylidene-5-chloro-3-cyclohexylcyclohex-3-ene-1,2-diol

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