(1S,3S,4S)-5-tert-butyloxycarbonyl-4-(tert-butyldiphenylsilyloxymethyl)-1-ethyloxycarbonyl-5-azaspiro[2.3]hexane

Base Information

Chemical Name:(1S,3S,4S)-5-tert-butyloxycarbonyl-4-(tert-butyldiphenylsilyloxymethyl)-1-ethyloxycarbonyl-5-azaspiro[2.3]hexane
CAS No.:1648572-46-6
Molecular Formula:C₃₀H₄₁NO₅Si
Molecular Weight:523.745
Hs Code.:

Synonyms:(1S,3S,4S)-5-tert-butyloxycarbonyl-4-(tert-butyldiphenylsilyloxymethyl)-1-ethyloxycarbonyl-5-azaspiro[2.3]hexane

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1S,3S,4S)-5-tert-butyloxycarbonyl-4-(tert-butyldiphenylsilyloxymethyl)-1-ethyloxycarbonyl-5-azaspiro[2.3]hexane

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Technology Process of (1S,3S,4S)-5-tert-butyloxycarbonyl-4-(tert-butyldiphenylsilyloxymethyl)-1-ethyloxycarbonyl-5-azaspiro[2.3]hexane

There total 1 articles about (1S,3S,4S)-5-tert-butyloxycarbonyl-4-(tert-butyldiphenylsilyloxymethyl)-1-ethyloxycarbonyl-5-azaspiro[2.3]hexane 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:

: 623-73-4
diazoacetic acid ethyl ester

: 1648572-35-3
(2S)-1-(tert-butyloxycarbonyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-methylideneazetidine

: (4S)-5-tert-butyloxycarbonyl-4-(tert-butyldiphenylsilyloxymethyl)-1-ethyloxycarbonyl-5-azaspiro[2.3]hexane

: 1648572-46-6
(1S,3S,4S)-5-tert-butyloxycarbonyl-4-(tert-butyldiphenylsilyloxymethyl)-1-ethyloxycarbonyl-5-azaspiro[2.3]hexane

: 1648572-37-5
(1R,3R,4S)-5-tert-butyloxycarbonyl-4-(tert-butyldiphenylsilyloxymethyl)-1-ethyloxycarbonyl-5-azaspiro[2.3]hexane

Guidance literature:: (2S)-1-(tert-butyloxycarbonyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-methylideneazetidine; With dirhodium tetraacetate; In dichloromethane; for 0.5h; Inert atmosphere; Reflux;

diazoacetic acid ethyl ester; In dichloromethane; for 69h; Solvent; Concentration; Overall yield = 60 %; Overall yield = 0.18 g; diastereoselective reaction; Inert atmosphere; Reflux;
DOI:10.3762/bjoc.10.110

Reference yield: 66.0%

: 1648572-46-6
(1S,3S,4S)-5-tert-butyloxycarbonyl-4-(tert-butyldiphenylsilyloxymethyl)-1-ethyloxycarbonyl-5-azaspiro[2.3]hexane

: 1648572-48-8
5-tert-butyl 1-ethyl (1S,3S,4S)-4-(hydroxymethyl)-5-azaspiro[2.3]hexane-1,5-dicarboxylate

Guidance literature:: With triethylamine tris(hydrogen fluoride); triethylamine; In tetrahydrofuran; at 60 ℃; for 41h; Inert atmosphere;
DOI:10.3762/bjoc.10.110

Reference yield:

: 1648572-46-6
(1S,3S,4S)-5-tert-butyloxycarbonyl-4-(tert-butyldiphenylsilyloxymethyl)-1-ethyloxycarbonyl-5-azaspiro[2.3]hexane

: 1648572-49-9
(1S,3S,4S)-5-(tert-butoxycarbonyl)-1-(ethoxycarbonyl)-5-azaspiro[2.3]hexane-4-carboxylic acid

Guidance literature:: Multi-step reaction with 2 steps

1: triethylamine; triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 41 h / 60 °C / Inert atmosphere

2: chromic acid / acetone / 2 h / 0 - 20 °C / Inert atmosphere

With chromic acid; triethylamine tris(hydrogen fluoride); triethylamine; In tetrahydrofuran; acetone; 2: |Jones Oxidation;
DOI:10.3762/bjoc.10.110