tert-butyl (2S,3R)-1-(3-bromophenyl)-3-(tert-butyldimethylsilyloxy)-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)-1-(3-bromophenyl)-3-(tert-butyldimethylsilyloxy)-4-((S)-6′-neopentyl-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-b]pyridine]-4′-ylamino)butan-2-ylcarbamate
CAS No.:1373756-41-2
Molecular Formula:C₃₇H₅₈BrN₃O₄Si
Molecular Weight:716.875
Hs Code.:

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

There total 13 articles about tert-butyl (2S,3R)-1-(3-bromophenyl)-3-(tert-butyldimethylsilyloxy)-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:

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

: tert-butyl (2S,3S)-1-(3-bromophenyl)-3-(tertbutyldimethylsilyloxy)-4-oxobutan-2-ylcarbamate

: 1373756-41-2
tert-butyl (2S,3R)-1-(3-bromophenyl)-3-(tert-butyldimethylsilyloxy)-4-((S)-6′-neopentyl-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-b]pyridine]-4′-ylamino)butan-2-ylcarbamate

Guidance literature:: With sodium tris(acetoxy)borohydride; trimethyl orthoformate; In dichloromethane; at 23 ℃; for 2h;
DOI:10.1021/jm300118s

Reference yield:

: 1-(prop-2-en-1-yl)cyclobutanol

: 1373756-41-2
tert-butyl (2S,3R)-1-(3-bromophenyl)-3-(tert-butyldimethylsilyloxy)-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 8 steps

1.1: triethylamine / dichloromethane / 0.5 h / Cooling with ice

2.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; water; tert-butyl alcohol / 2 h / 20 °C

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

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

5.1: n-butyllithium; 2,2,6,6-tetramethyl-piperidine / tetrahydrofuran; toluene / 0.5 h / 0 °C

5.2: 0.5 h / -65 - -10 °C

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

7.1: hydrogenchloride / dichloromethane / 1 h / 25 °C

8.1: trimethyl orthoformate; sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 23 °C

With 2,2,6,6-tetramethyl-piperidine; hydrogenchloride; sodium periodate; osmium(VIII) oxide; n-butyllithium; sodium tris(acetoxy)borohydride; copper(II) sulfate; 4-methylmorpholine N-oxide; triethylamine; cesium fluoride; trimethyl orthoformate; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; toluene; tert-butyl alcohol;
DOI:10.1021/jm300118s

Reference yield:

: 1227784-58-8
(1-allylcyclobutoxy)(tert-butyl)dimethylsilane

: 1373756-41-2
tert-butyl (2S,3R)-1-(3-bromophenyl)-3-(tert-butyldimethylsilyloxy)-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 7 steps

1.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; water; tert-butyl alcohol / 2 h / 20 °C

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

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

4.1: n-butyllithium; 2,2,6,6-tetramethyl-piperidine / tetrahydrofuran; toluene / 0.5 h / 0 °C

4.2: 0.5 h / -65 - -10 °C

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

6.1: hydrogenchloride / dichloromethane / 1 h / 25 °C

7.1: trimethyl orthoformate; sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 23 °C

With 2,2,6,6-tetramethyl-piperidine; hydrogenchloride; sodium periodate; osmium(VIII) oxide; n-butyllithium; sodium tris(acetoxy)borohydride; copper(II) sulfate; 4-methylmorpholine N-oxide; cesium fluoride; trimethyl orthoformate; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; toluene; tert-butyl alcohol;
DOI:10.1021/jm300118s