(5S,6S,7S,7aS)-6,7-dihydroxy-5-{4-(p-tolyl)butyl}tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one

Base Information

Chemical Name:(5S,6S,7S,7aS)-6,7-dihydroxy-5-{4-(p-tolyl)butyl}tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one
CAS No.:1618658-01-7
Molecular Formula:C₁₇H₂₃NO₄
Molecular Weight:305.374
Hs Code.:

Synonyms:(5S,6S,7S,7aS)-6,7-dihydroxy-5-{4-(p-tolyl)butyl}tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one

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Chemical Property of (5S,6S,7S,7aS)-6,7-dihydroxy-5-{4-(p-tolyl)butyl}tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one

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Technology Process of (5S,6S,7S,7aS)-6,7-dihydroxy-5-{4-(p-tolyl)butyl}tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one

There total 4 articles about (5S,6S,7S,7aS)-6,7-dihydroxy-5-{4-(p-tolyl)butyl}tetrahydropyrrolo[1,2-c]oxazol-3(1H)-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: 77.0%

: 1618657-97-8
(1aR,1bS,6S,6aS)-6-{4-(p-tolyl)butyl}tetrahydrooxireno[2',3':3,4]pyrrolo[1,2-c]oxazol-4(1aH)-one

: 1618658-01-7
(5S,6S,7S,7aS)-6,7-dihydroxy-5-{4-(p-tolyl)butyl}tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one

Guidance literature:: With trifluoroacetic acid; In tetrahydrofuran; water; at 80 ℃; for 72h;
DOI:10.1016/j.bmcl.2014.06.001

Reference yield:

: 1618657-90-1
(5S,7aR)-5-{4-(p-tolyl)butyl}-1,7a-dihydropyrrolo[1,2-c]oxazol-3(5H)-one

: 1618658-01-7
(5S,6S,7S,7aS)-6,7-dihydroxy-5-{4-(p-tolyl)butyl}tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one

Guidance literature:: Multi-step reaction with 2 steps

1: Oxone; ethylenediaminetetraacetic acid; 1,1,1-trifluoro-2-propanone; sodium hydrogencarbonate / acetonitrile; water / 4 h / 0 °C

2: trifluoroacetic acid / tetrahydrofuran; water / 72 h / 80 °C

With Oxone; ethylenediaminetetraacetic acid; 1,1,1-trifluoro-2-propanone; sodium hydrogencarbonate; trifluoroacetic acid; In tetrahydrofuran; water; acetonitrile;
DOI:10.1016/j.bmcl.2014.06.001

Reference yield:

: 54540-53-3
1-(3-bromopropyl)-4-methylbenzene

: 1618658-01-7
(5S,6S,7S,7aS)-6,7-dihydroxy-5-{4-(p-tolyl)butyl}tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one

Guidance literature:: Multi-step reaction with 4 steps

1: iodine; zinc / N,N-dimethyl acetamide / 3 h / 20 - 80 °C

2: bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; 2,6-bis((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)pyridine / N,N-dimethyl acetamide / 20 h / 20 °C / Inert atmosphere

3: Oxone; ethylenediaminetetraacetic acid; 1,1,1-trifluoro-2-propanone; sodium hydrogencarbonate / acetonitrile; water / 4 h / 0 °C

4: trifluoroacetic acid / tetrahydrofuran; water / 72 h / 80 °C

With Oxone; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; ethylenediaminetetraacetic acid; 1,1,1-trifluoro-2-propanone; iodine; sodium hydrogencarbonate; 2,6-bis((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)pyridine; trifluoroacetic acid; zinc; In tetrahydrofuran; N,N-dimethyl acetamide; water; acetonitrile; 2: |Negishi Coupling;
DOI:10.1016/j.bmcl.2014.06.001