tert-butyl (2R,3S,4S,5R,αR)-2-hydroxy-3-[N-but-3'-enyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidenehept-6-enoate

Base Information

Chemical Name:tert-butyl (2R,3S,4S,5R,αR)-2-hydroxy-3-[N-but-3'-enyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidenehept-6-enoate
CAS No.:1273232-24-8
Molecular Formula:C₂₆H₃₉NO₅
Molecular Weight:445.599
Hs Code.:

Synonyms:tert-butyl (2R,3S,4S,5R,αR)-2-hydroxy-3-[N-but-3'-enyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidenehept-6-enoate

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Chemical Property of tert-butyl (2R,3S,4S,5R,αR)-2-hydroxy-3-[N-but-3'-enyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidenehept-6-enoate

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Technology Process of tert-butyl (2R,3S,4S,5R,αR)-2-hydroxy-3-[N-but-3'-enyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidenehept-6-enoate

There total 4 articles about tert-butyl (2R,3S,4S,5R,αR)-2-hydroxy-3-[N-but-3'-enyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidenehept-6-enoate 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: 56.0%

: 177944-16-0
(R)-N-(but-3-en-1-yl)-N-(α-methylbenzyl)amine

: 1085845-83-5
tert-butyl (2E,4S,5R)-4,5-O-isopropylidene-hepta-2,6-dienoate

: 1273232-46-4
tert-butyl (3S,4S,5R,αR)-3-[N-but-3'-enyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidenehept-6-enoate

: 1273232-24-8
tert-butyl (2R,3S,4S,5R,αR)-2-hydroxy-3-[N-but-3'-enyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidenehept-6-enoate

Guidance literature:: (R)-N-(but-3-en-1-yl)-N-(α-methylbenzyl)amine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃;

tert-butyl (2E,4S,5R)-4,5-O-isopropylidene-hepta-2,6-dienoate; In tetrahydrofuran; hexane; at -78 ℃;

With (1R)-(?)-(10-camphorsulfonyl)oxaziridine; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 12h; optical yield given as %de; diastereoselective reaction;
DOI:10.1021/ol103090z

Reference yield:

: 532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7
D-Ribose

: 1273232-46-4
tert-butyl (3S,4S,5R,αR)-3-[N-but-3'-enyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidenehept-6-enoate

: 1273232-24-8
tert-butyl (2R,3S,4S,5R,αR)-2-hydroxy-3-[N-but-3'-enyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidenehept-6-enoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: hydrogenchloride / water / Reflux

2.1: 1H-imidazole; iodine; triphenylphosphine / toluene; acetonitrile / 1 h / 60 °C

3.1: n-butyllithium / diethyl ether; hexane / -78 - 20 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C

4.2: -78 °C

4.3: 12 h / -78 - 20 °C

With 1H-imidazole; hydrogenchloride; n-butyllithium; iodine; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; water; toluene; acetonitrile;
DOI:10.1021/ol103090z

Reference yield:

: 4099-85-8,828937-29-7
((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

: 1273232-46-4
tert-butyl (3S,4S,5R,αR)-3-[N-but-3'-enyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidenehept-6-enoate

: 1273232-24-8
tert-butyl (2R,3S,4S,5R,αR)-2-hydroxy-3-[N-but-3'-enyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidenehept-6-enoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1H-imidazole; iodine; triphenylphosphine / toluene; acetonitrile / 1 h / 60 °C

2.1: n-butyllithium / diethyl ether; hexane / -78 - 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C

3.2: -78 °C

3.3: 12 h / -78 - 20 °C

With 1H-imidazole; n-butyllithium; iodine; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; toluene; acetonitrile;
DOI:10.1021/ol103090z