tert-butyl (2S,3R)-3-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxyphenyl)-4-((S)-6′-neopentyl-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-b]pyridine]-4′-ylamino)butan-2-ylcarbamate

Base Information

Chemical Name:tert-butyl (2S,3R)-3-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxyphenyl)-4-((S)-6′-neopentyl-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-b]pyridine]-4′-ylamino)butan-2-ylcarbamate
CAS No.:1373754-55-2
Molecular Formula:C₃₉H₆₃N₃O₆Si
Molecular Weight:698.031
Hs Code.:

tert-butyl (2S,3R)-3-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxyphenyl)-4-((S)-6′-neopentyl-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-b]pyridine]-4′-ylamino)butan-2-ylcarbamate

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Chemical Property of tert-butyl (2S,3R)-3-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxyphenyl)-4-((S)-6′-neopentyl-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-b]pyridine]-4′-ylamino)butan-2-ylcarbamate

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Technology Process of tert-butyl (2S,3R)-3-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxyphenyl)-4-((S)-6′-neopentyl-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-b]pyridine]-4′-ylamino)butan-2-ylcarbamate

There total 11 articles about tert-butyl (2S,3R)-3-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxyphenyl)-4-((S)-6′-neopentyl-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-b]pyridine]-4′-ylamino)butan-2-ylcarbamate 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: 100.0%

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

: 1373754-33-6
tert-butyl [(2S,3S)-3-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxyphenyl)-4-oxobutan-2-yl]carbamate

: 1373754-55-2
tert-butyl (2S,3R)-3-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxyphenyl)-4-((S)-6′-neopentyl-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-b]pyridine]-4′-ylamino)butan-2-ylcarbamate

Guidance literature:: (S)-6′-neopentyl-3′,4′-dihydrospiro-[cyclobutane-1,2′-pyrano[2,3-b]pyridin]-4′-amine; tert-butyl [(2S,3S)-3-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxyphenyl)-4-oxobutan-2-yl]carbamate; 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:

: 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

: 1373754-55-2
tert-butyl (2S,3R)-3-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxyphenyl)-4-((S)-6′-neopentyl-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-b]pyridine]-4′-ylamino)butan-2-ylcarbamate

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

Reference yield:

: 939411-88-8
3-(1-(tert-butyldimethylsilyloxy)cyclobutyl)propane-1,2-diol

: 1373754-55-2
tert-butyl (2S,3R)-3-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxyphenyl)-4-((S)-6′-neopentyl-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-b]pyridine]-4′-ylamino)butan-2-ylcarbamate

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium periodate / tetrahydrofuran; water; tert-butyl alcohol / 1.5 h

2.1: copper(II) sulfate / dichloromethane / 16 h / 20 °C

3.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / tetrahydrofuran; toluene / 0.75 h / -78 - 0 °C

3.2: 0.5 h / -78 - -10 °C

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

5.1: hydrogenchloride / dichloromethane; water / 25 °C

6.1: trimethyl orthoformate / dichloromethane / 0.33 h

6.2: 2 h

With 2,2,6,6-tetramethyl-piperidine; hydrogenchloride; sodium periodate; n-butyllithium; copper(II) sulfate; cesium fluoride; trimethyl orthoformate; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; toluene; tert-butyl alcohol;
DOI:10.1021/jm300119p