(4S,5R)-tertbutyl 4-(3,4-bis(difluoromethoxy)benzyl)-2,2-dimethyl-5-(((S)-6′-neopentyl-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-b]-pyridine]-4′-ylamino)methyl)oxazolidine-3-carboxylate

Base Information

Chemical Name:(4S,5R)-tertbutyl 4-(3,4-bis(difluoromethoxy)benzyl)-2,2-dimethyl-5-(((S)-6′-neopentyl-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-b]-pyridine]-4′-ylamino)methyl)oxazolidine-3-carboxylate
CAS No.:1373754-59-6
Molecular Formula:C₃₆H₄₉F₄N₃O₆
Molecular Weight:695.795
Hs Code.:

(4S,5R)-tertbutyl 4-(3,4-bis(difluoromethoxy)benzyl)-2,2-dimethyl-5-(((S)-6′-neopentyl-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-b]-pyridine]-4′-ylamino)methyl)oxazolidine-3-carboxylate

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Chemical Property of (4S,5R)-tertbutyl 4-(3,4-bis(difluoromethoxy)benzyl)-2,2-dimethyl-5-(((S)-6′-neopentyl-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-b]-pyridine]-4′-ylamino)methyl)oxazolidine-3-carboxylate

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Technology Process of (4S,5R)-tertbutyl 4-(3,4-bis(difluoromethoxy)benzyl)-2,2-dimethyl-5-(((S)-6′-neopentyl-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-b]-pyridine]-4′-ylamino)methyl)oxazolidine-3-carboxylate

There total 16 articles about (4S,5R)-tertbutyl 4-(3,4-bis(difluoromethoxy)benzyl)-2,2-dimethyl-5-(((S)-6′-neopentyl-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-b]-pyridine]-4′-ylamino)methyl)oxazolidine-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: 97.0%

: 939411-93-5
(S)-6′-neopentyl-3′,4′-dihydrospiro-[cyclobutane-1,2′-pyrano[2,3-b]pyridin]-4′-amine

: 1373754-51-8
(4S)-tert-butyl 4-(3,4-bis(difluoromethoxy)benzyl)-5-formyl-2,2-dimethyloxazolidine-3-carboxylate

: 1373754-59-6
(4S,5R)-tertbutyl 4-(3,4-bis(difluoromethoxy)benzyl)-2,2-dimethyl-5-(((S)-6′-neopentyl-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-b]-pyridine]-4′-ylamino)methyl)oxazolidine-3-carboxylate

Guidance literature:: (S)-6′-neopentyl-3′,4′-dihydrospiro-[cyclobutane-1,2′-pyrano[2,3-b]pyridin]-4′-amine; (4S)-tert-butyl 4-(3,4-bis(difluoromethoxy)benzyl)-5-formyl-2,2-dimethyloxazolidine-3-carboxylate; With trimethyl orthoformate; In dichloromethane; for 0.333333h;

With sodium tris(acetoxy)borohydride; rochelle salt; In dichloromethane; for 2h;
DOI:10.1021/jm300119p

Reference yield:

: 1373320-14-9
(S)-N-((S)-2-(1-(tert-butyldimethylsilyloxy)cyclobutyl)-1-(2-fluoro-5-neopentylpyridin-3-yl)ethyl)-2-methylpropane-2-sulfinamide

: 1373754-59-6
(4S,5R)-tertbutyl 4-(3,4-bis(difluoromethoxy)benzyl)-2,2-dimethyl-5-(((S)-6′-neopentyl-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-b]-pyridine]-4′-ylamino)methyl)oxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: cesium fluoride / dimethyl sulfoxide / 15 h / 120 °C

2.1: hydrogenchloride / dichloromethane; water / 25 °C

3.1: trimethyl orthoformate / dichloromethane / 0.33 h

3.2: 2 h

With hydrogenchloride; cesium fluoride; trimethyl orthoformate; In dichloromethane; water; dimethyl sulfoxide;
DOI:10.1021/jm300119p

Reference yield:

: 1373754-63-2
(R)-2-methyl-N-((S)-6'-neopentyl-3',4'-dihydrospiro[cyclobutane-1,2'-pyrano[2,3-b]pyridine]-4'-yl)propane-2-sulfinamide

: 1373754-59-6
(4S,5R)-tertbutyl 4-(3,4-bis(difluoromethoxy)benzyl)-2,2-dimethyl-5-(((S)-6′-neopentyl-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-b]-pyridine]-4′-ylamino)methyl)oxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: hydrogenchloride / dichloromethane; water / 25 °C

2.1: trimethyl orthoformate / dichloromethane / 0.33 h

2.2: 2 h

With hydrogenchloride; trimethyl orthoformate; In dichloromethane; water;
DOI:10.1021/jm300119p