(4S,5R,1'R,αR)-4-[N-benzyl-N-(α-methylbenzyl)amino]-5-(1-hydroxyethyl)dihydrofuran-2(3H)-one

Base Information

Chemical Name:(4S,5R,1'R,αR)-4-[N-benzyl-N-(α-methylbenzyl)amino]-5-(1-hydroxyethyl)dihydrofuran-2(3H)-one
CAS No.:178976-44-8
Molecular Formula:C₂₁H₂₅NO₃
Molecular Weight:339.434
Hs Code.:

Synonyms:(4S,5R,1'R,αR)-4-[N-benzyl-N-(α-methylbenzyl)amino]-5-(1-hydroxyethyl)dihydrofuran-2(3H)-one

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Chemical Property of (4S,5R,1'R,αR)-4-[N-benzyl-N-(α-methylbenzyl)amino]-5-(1-hydroxyethyl)dihydrofuran-2(3H)-one

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Technology Process of (4S,5R,1'R,αR)-4-[N-benzyl-N-(α-methylbenzyl)amino]-5-(1-hydroxyethyl)dihydrofuran-2(3H)-one

There total 15 articles about (4S,5R,1'R,αR)-4-[N-benzyl-N-(α-methylbenzyl)amino]-5-(1-hydroxyethyl)dihydrofuran-2(3H)-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: 63.0%

: 184840-85-5
tert-Butyl (3S,αR)-(E)-3-[N-benzyl-N-(α-methylbenzyl)amino]hex-4-enoate

: 178976-44-8
(4S,5R,1'R,αR)-4-[N-benzyl-N-(α-methylbenzyl)amino]-5-(1-hydroxyethyl)dihydrofuran-2(3H)-one

: tert-Butyl (3S,4R,5R,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-dihydroxyhexanoate

Guidance literature:: tert-Butyl (3S,αR)-(E)-3-[N-benzyl-N-(α-methylbenzyl)amino]hex-4-enoate; With osmium(VIII) oxide; N,N,N,N,-tetramethylethylenediamine; In dichloromethane; at -78 - 20 ℃; for 1.25h;

With ethylenediamine; In dichloromethane; at 20 ℃; for 16h; optical yield given as %de; diastereoselective reaction;
DOI:10.1021/ol200717n

Reference yield: 48.0%

: 178976-42-6
Methyl (3S,αR)-(E)-3-[N-benzyl-N-(α-methylbenzyl)amino]hex-4-enoate

: 178976-45-9
(3S,4S,5S,αR)-3-[N-Benzyl-N-(α-methylbenzyl)amino]-5-hydroxyhexano-4-lactone

: 178976-44-8
(4S,5R,1'R,αR)-4-[N-benzyl-N-(α-methylbenzyl)amino]-5-(1-hydroxyethyl)dihydrofuran-2(3H)-one

Guidance literature:: With osmium(VIII) oxide; potassium carbonate; potassium hexacyanoferrate(III); In water; tert-butyl alcohol; at 20 ℃;
DOI:10.1039/a907017f

Reference yield:

: 100-52-7
benzaldehyde

: 178976-44-8
(4S,5R,1'R,αR)-4-[N-benzyl-N-(α-methylbenzyl)amino]-5-(1-hydroxyethyl)dihydrofuran-2(3H)-one

: tert-Butyl (3S,4R,5R,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-dihydroxyhexanoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium tetrahydroborate / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

2.2: 2 h / -78 °C / Inert atmosphere

2.3: -78 - 20 °C / Inert atmosphere

3.1: osmium(VIII) oxide; N,N,N,N,-tetramethylethylenediamine / dichloromethane / 1.25 h / -78 - 20 °C

3.2: 16 h / 20 °C

With sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; hexane; dichloromethane; 3.1: Donohoe oxidation / 3.2: Donohoe oxidation;
DOI:10.1021/ol200717n