tert-butyl (3S,4S,5S,αR)-3-[N-but-3′-enyl-N-(α-methyl-p-methoxybenzyl)amino]-4,5-dihydroxy-4,5-O-isopropylidenehept-6-enoate

Base Information

Chemical Name:tert-butyl (3S,4S,5S,αR)-3-[N-but-3′-enyl-N-(α-methyl-p-methoxybenzyl)amino]-4,5-dihydroxy-4,5-O-isopropylidenehept-6-enoate
CAS No.:1432590-55-0
Molecular Formula:C₂₇H₄₁NO₅
Molecular Weight:459.626
Hs Code.:

Synonyms:tert-butyl (3S,4S,5S,αR)-3-[N-but-3′-enyl-N-(α-methyl-p-methoxybenzyl)amino]-4,5-dihydroxy-4,5-O-isopropylidenehept-6-enoate

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Chemical Property of tert-butyl (3S,4S,5S,αR)-3-[N-but-3′-enyl-N-(α-methyl-p-methoxybenzyl)amino]-4,5-dihydroxy-4,5-O-isopropylidenehept-6-enoate

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Technology Process of tert-butyl (3S,4S,5S,αR)-3-[N-but-3′-enyl-N-(α-methyl-p-methoxybenzyl)amino]-4,5-dihydroxy-4,5-O-isopropylidenehept-6-enoate

There total 9 articles about tert-butyl (3S,4S,5S,αR)-3-[N-but-3′-enyl-N-(α-methyl-p-methoxybenzyl)amino]-4,5-dihydroxy-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: 65.0%

: 1258980-78-7
(R)-N-but-3-enyl-N-(α-methyl-p-methoxybenzyl)amine

: 1393792-82-9
tert-butyl (S,S,E)-4,5-dihydroxy-4,5-O-isopropylidenehepta-2,6-dienoate

: 1432590-55-0
tert-butyl (3S,4S,5S,αR)-3-[N-but-3′-enyl-N-(α-methyl-p-methoxybenzyl)amino]-4,5-dihydroxy-4,5-O-isopropylidenehept-6-enoate

Guidance literature:: (R)-N-but-3-enyl-N-(α-methyl-p-methoxybenzyl)amine; With n-butyllithium; In hexane; at -78 ℃; for 0.5h;

tert-butyl (S,S,E)-4,5-dihydroxy-4,5-O-isopropylidenehepta-2,6-dienoate; In tetrahydrofuran; at -78 ℃; for 2h;
DOI:10.1039/c3ob40205c

Reference yield: 58.0%

: 1258980-78-7
(R)-N-but-3-enyl-N-(α-methyl-p-methoxybenzyl)amine

: 1393792-82-9
tert-butyl (S,S,E)-4,5-dihydroxy-4,5-O-isopropylidenehepta-2,6-dienoate

: 1432590-55-0
tert-butyl (3S,4S,5S,αR)-3-[N-but-3′-enyl-N-(α-methyl-p-methoxybenzyl)amino]-4,5-dihydroxy-4,5-O-isopropylidenehept-6-enoate

: 1432590-56-1
tert-butyl (2R,3S,4S,5S,αR)-2,4,5-trihydroxy-3-[N-but-3′-enyl-N-(α-methyl-p-methoxybenzyl)amino]-4,5-O-isopropylidenehept-6-enoate

Guidance literature:: (R)-N-but-3-enyl-N-(α-methyl-p-methoxybenzyl)amine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

tert-butyl (S,S,E)-4,5-dihydroxy-4,5-O-isopropylidenehepta-2,6-dienoate; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

With (-)-CSO; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 12h;
DOI:10.1039/c3ob40205c

Reference yield:

: 207123-20-4
(S,S)-2,2-dimethyl-4-(tert-butyldimethylsilyloxy)methyl-5-hydroxymethyl-1,3-dioxolane

: 1432590-55-0
tert-butyl (3S,4S,5S,αR)-3-[N-but-3′-enyl-N-(α-methyl-p-methoxybenzyl)amino]-4,5-dihydroxy-4,5-O-isopropylidenehept-6-enoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2.5 h / 0 °C

2.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 1 h / -78 °C

2.2: 0.5 h / -78 - 20 °C

3.1: 12 h / 20 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

4.2: 2 h / -78 °C

4.3: 12 h / -78 - 20 °C

With n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; 2.1: |Swern Oxidation / 3.1: |Wittig-Horner Reaction;
DOI:10.1039/c3ob40205c