tert-butyl (3R,4R,5S,6R,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5,6,7-tetrahydroxy-4,5,6,7-di-O-isopropylideneheptanoate

Base Information

Chemical Name:tert-butyl (3R,4R,5S,6R,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5,6,7-tetrahydroxy-4,5,6,7-di-O-isopropylideneheptanoate
CAS No.:1454884-16-2
Molecular Formula:C₃₂H₄₅NO₆
Molecular Weight:539.712
Hs Code.:

Synonyms:tert-butyl (3R,4R,5S,6R,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5,6,7-tetrahydroxy-4,5,6,7-di-O-isopropylideneheptanoate

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Chemical Property of tert-butyl (3R,4R,5S,6R,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5,6,7-tetrahydroxy-4,5,6,7-di-O-isopropylideneheptanoate

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Technology Process of tert-butyl (3R,4R,5S,6R,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5,6,7-tetrahydroxy-4,5,6,7-di-O-isopropylideneheptanoate

There total 5 articles about tert-butyl (3R,4R,5S,6R,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5,6,7-tetrahydroxy-4,5,6,7-di-O-isopropylideneheptanoate 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: 73.0%

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

: 1454884-08-2
tert-butyl (4R,5S,6R,E)-4,5,6,7-tetrahydroxy-4,5,6,7-di-O-isopropylidenehept-2-enoate

: 1454884-16-2
tert-butyl (3R,4R,5S,6R,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5,6,7-tetrahydroxy-4,5,6,7-di-O-isopropylideneheptanoate

Guidance literature:: (S)-N-benzyl-1-phenylethylamine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

tert-butyl (4R,5S,6R,E)-4,5,6,7-tetrahydroxy-4,5,6,7-di-O-isopropylidenehept-2-enoate; In tetrahydrofuran; hexane; at -78 ℃; for 2h; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2013.07.096

Reference yield:

: C₁₇H₂₈O₆

: 38235-77-7
(R)-N-benzyl-1-phenylethylamine

: 1454884-16-2
tert-butyl (3R,4R,5S,6R,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5,6,7-tetrahydroxy-4,5,6,7-di-O-isopropylideneheptanoate

: tert-butyl (2R,3R,4R,5S,6R,αS)-2,4,5,6,7-pentahydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5,6,7-di-O-isopropylideneheptanoate

: C₃₂H₄₅NO₇

Guidance literature:: (R)-N-benzyl-1-phenylethylamine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

C₁₇H₂₈O₆; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

With (1S)-(+)-(10-camphorsulfonyl)-oxaziridine; In tetrahydrofuran; hexane; at 20 ℃; for 12h; Reagent/catalyst;
DOI:10.1016/j.tet.2014.06.019

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-arabinofuranose

: 1454884-16-2
tert-butyl (3R,4R,5S,6R,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5,6,7-tetrahydroxy-4,5,6,7-di-O-isopropylideneheptanoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1,4-dioxane / 18 h / 50 - 90 °C

2.1: toluene-4-sulfonic acid / 18 h / 20 °C

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

3.2: 2 h / -78 °C / Inert atmosphere

With n-butyllithium; toluene-4-sulfonic acid; In tetrahydrofuran; 1,4-dioxane; hexane; 1.1: |Wittig Olefination;
DOI:10.1016/j.tet.2013.07.096