3,8-Dioxa-7-azabicyclo[4.3.1]decan-10-one, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-(hydroxymethyl)-2,2-dimethyl-7 -(phenylmethyl)-, (1R,4S,5S,6S)-

Base Information

Chemical Name:3,8-Dioxa-7-azabicyclo[4.3.1]decan-10-one, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-(hydroxymethyl)-2,2-dimethyl-7 -(phenylmethyl)-, (1R,4S,5S,6S)-
CAS No.:870461-36-2
Molecular Formula:C23H37NO5Si
Molecular Weight:435.636
Hs Code.:

3,8-Dioxa-7-azabicyclo[4.3.1]decan-10-one,
5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-(hydroxymethyl)-2,2-dimethyl-7
-(phenylmethyl)-, (1R,4S,5S,6S)-

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Chemical Property of 3,8-Dioxa-7-azabicyclo[4.3.1]decan-10-one, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-(hydroxymethyl)-2,2-dimethyl-7 -(phenylmethyl)-, (1R,4S,5S,6S)-

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Technology Process of 3,8-Dioxa-7-azabicyclo[4.3.1]decan-10-one, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-(hydroxymethyl)-2,2-dimethyl-7 -(phenylmethyl)-, (1R,4S,5S,6S)-

There total 3 articles about 3,8-Dioxa-7-azabicyclo[4.3.1]decan-10-one, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-(hydroxymethyl)-2,2-dimethyl-7 -(phenylmethyl)-, (1R,4S,5S,6S)- 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: 55.0%

: 870461-26-0
(3S,1'S,4''S)-2-benzyl-1'-[(tert-butyldimethylsiloxy)-(2'',2''-dimethyl-1'',3''-dioxolan-4''-yl)methyl]-4-[2'''-(trimethylsilyl)ethoxy]-3,6-dihydro-2H-1,2-oxazine

: 870461-36-2
(1R,4R,5R,6S)-7-benzyl-5-(tert-butyldimethylsilyloxy)-4-hydroxymethyl-2,2-dimethyl-3,8-dioxa-7-aza-bicyclo[4.3.1]decan-10-one

Guidance literature:: With tin(IV) chloride; In acetonitrile; at -30 - 20 ℃; for 6h;
DOI:10.1002/anie.200501127

Reference yield:

: C₂₀H₃₃NO₄Si

: 870461-36-2
(1R,4R,5R,6S)-7-benzyl-5-(tert-butyldimethylsilyloxy)-4-hydroxymethyl-2,2-dimethyl-3,8-dioxa-7-aza-bicyclo[4.3.1]decan-10-one

Guidance literature:: Multi-step reaction with 2 steps

1: 71 percent / tetrahydrofuran / 2 h / -78 °C

2: 55 percent / SnCl₄ / acetonitrile / 6 h / -30 - 20 °C

With tin(IV) chloride; In tetrahydrofuran; acetonitrile;
DOI:10.1002/anie.200501127

Reference yield:

: 870461-25-9
C₂₀H₃₃NO₄Si

: 870461-36-2
(1R,4R,5R,6S)-7-benzyl-5-(tert-butyldimethylsilyloxy)-4-hydroxymethyl-2,2-dimethyl-3,8-dioxa-7-aza-bicyclo[4.3.1]decan-10-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -40 °C / Inert atmosphere

1.2: 2.5 h / -78 °C / Inert atmosphere

2.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 5.5 h / -5 - 0 °C / Inert atmosphere

With n-butyllithium; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.3762/bjoc.10.17