tert-butyl (3S,4R,αS)-4-(N-benzyl-N-α-methylbenzylamino)tetrahydrofuran-3-carboxylate

Base Information

Chemical Name:tert-butyl (3S,4R,αS)-4-(N-benzyl-N-α-methylbenzylamino)tetrahydrofuran-3-carboxylate
CAS No.:797038-51-8
Molecular Formula:C₂₄H₃₁NO₃
Molecular Weight:381.515
Hs Code.:

Synonyms:tert-butyl (3S,4R,αS)-4-(N-benzyl-N-α-methylbenzylamino)tetrahydrofuran-3-carboxylate

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Chemical Property of tert-butyl (3S,4R,αS)-4-(N-benzyl-N-α-methylbenzylamino)tetrahydrofuran-3-carboxylate

Chemical Property:

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Technology Process of tert-butyl (3S,4R,αS)-4-(N-benzyl-N-α-methylbenzylamino)tetrahydrofuran-3-carboxylate

There total 5 articles about tert-butyl (3S,4R,αS)-4-(N-benzyl-N-α-methylbenzylamino)tetrahydrofuran-3-carboxylate 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%

: 17480-69-2
(S)-N-benzyl-1-phenylethylamine

: 797038-34-7
tert-butyl 2,5-dihydrofuran-3-carboxylate

: 797038-52-9
tert-butyl (3R,4R,αS)-4-(N-benzyl-N-α-methylbenzylamino)tetrahydrofuran-3-carboxylate

: 797038-51-8
tert-butyl (3S,4R,αS)-4-(N-benzyl-N-α-methylbenzylamino)tetrahydrofuran-3-carboxylate

Guidance literature:: (S)-N-benzyl-1-phenylethylamine; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h;

tert-butyl 2,5-dihydrofuran-3-carboxylate; In tetrahydrofuran; at -78 ℃; for 0.166667h;
DOI:10.1039/b407558g

Reference yield: 17.0%

: 17480-69-2
(S)-N-benzyl-1-phenylethylamine

: 797038-34-7
tert-butyl 2,5-dihydrofuran-3-carboxylate

: 797038-51-8
tert-butyl (3S,4R,αS)-4-(N-benzyl-N-α-methylbenzylamino)tetrahydrofuran-3-carboxylate

: tert-butyl (3S,4R,αS)-4-(N-benzyl-N-α-methylbenzylamino)-3-(2'-oxo-2',5'-dihydrofuran-3'-ylmethyl)tetrahydrofuran-3-carboxylate

: di-tert-butyl (3S,4R,3'S,4'S,αS)-4-(N-benzyl-N-α-methylbenzylamino)tetrahydro-[3,3']-bifuranyl-3,4'-dicarboxylate

: tert-butyl (3S,4R,3'S,4'R,αS,α'S)-4-(N-benzyl-N-α-methylbenzylamino)-3-[4'-(N-benzyl-N-α-methylbenzylamino)-2'-oxotetrahydrofuran-3'-ylmethyl]tetrahydrofuran-3-carboxylate

Guidance literature:: (S)-N-benzyl-1-phenylethylamine; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h;

tert-butyl 2,5-dihydrofuran-3-carboxylate; In tetrahydrofuran; at -78 ℃; for 3h; Further byproducts given;
DOI:10.1039/b407558g

Reference yield:

: 1663-39-4,25232-27-3
tert-Butyl acrylate

: 797038-51-8
tert-butyl (3S,4R,αS)-4-(N-benzyl-N-α-methylbenzylamino)tetrahydrofuran-3-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / diethyl ether / 0.5 h / 20 °C

1.2: 68 percent / dimethylsulfoxide / 0.5 h / 20 °C

2.1: 89 percent / NaBH₄ / propan-2-ol / 0 - 20 °C

3.1: 91 percent / PPh₃; DIAD / tetrahydrofuran / 20 °C

4.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C

4.2: 68 percent / tetrahydrofuran / 0.17 h / -78 °C

With sodium tetrahydroborate; n-butyllithium; di-isopropyl azodicarboxylate; sodium hydride; triphenylphosphine; In tetrahydrofuran; diethyl ether; isopropyl alcohol;
DOI:10.1039/b407558g