tert-butyl (2S,5S,6R)-2-[(benzyloxy)methyl]-6-{(1S,3S)-1-hydroxy-3-[(methylsulfonyl)oxy]nonyl}-1-azaspiro[4.5]decane-1-carboxylate

Base Information

Chemical Name:tert-butyl (2S,5S,6R)-2-[(benzyloxy)methyl]-6-{(1S,3S)-1-hydroxy-3-[(methylsulfonyl)oxy]nonyl}-1-azaspiro[4.5]decane-1-carboxylate
CAS No.:844698-94-8
Molecular Formula:C₃₂H₅₃NO₇S
Molecular Weight:595.841
Hs Code.:

Synonyms:tert-butyl (2S,5S,6R)-2-[(benzyloxy)methyl]-6-{(1S,3S)-1-hydroxy-3-[(methylsulfonyl)oxy]nonyl}-1-azaspiro[4.5]decane-1-carboxylate

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Chemical Property of tert-butyl (2S,5S,6R)-2-[(benzyloxy)methyl]-6-{(1S,3S)-1-hydroxy-3-[(methylsulfonyl)oxy]nonyl}-1-azaspiro[4.5]decane-1-carboxylate

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Technology Process of tert-butyl (2S,5S,6R)-2-[(benzyloxy)methyl]-6-{(1S,3S)-1-hydroxy-3-[(methylsulfonyl)oxy]nonyl}-1-azaspiro[4.5]decane-1-carboxylate

There total 8 articles about tert-butyl (2S,5S,6R)-2-[(benzyloxy)methyl]-6-{(1S,3S)-1-hydroxy-3-[(methylsulfonyl)oxy]nonyl}-1-azaspiro[4.5]decane-1-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: 73.0%

: 124-63-0
methanesulfonyl chloride

: 844698-93-7
tert-butyl (2S,5S,6R)-2-[(benzyloxy)methyl]-6-[(1S,3S)-1,3-dihydroxynonyl]-1-azaspiro[4.5]decane-1-carboxylate

: 844698-94-8
tert-butyl (2S,5S,6R)-2-[(benzyloxy)methyl]-6-{(1S,3S)-1-hydroxy-3-[(methylsulfonyl)oxy]nonyl}-1-azaspiro[4.5]decane-1-carboxylate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1021/ja040213e

Reference yield:

: 484061-51-0
tert-butyl (2S,5S,6S)-2-benzyloxymethyl-6-[(1E)-3-oxonon-1-enyl]-1-azaspiro[4.5]decane-1-carboxylate

: 844698-94-8
tert-butyl (2S,5S,6R)-2-[(benzyloxy)methyl]-6-{(1S,3S)-1-hydroxy-3-[(methylsulfonyl)oxy]nonyl}-1-azaspiro[4.5]decane-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 92 percent / LiAlH₄; (S)-1,1'-binaphthol; ethanol / tetrahydrofuran / 5 h / -78 °C

2: 68 percent / m-chloroperbenzoic acid; sodium hydrogen phosphate / CH₂Cl₂ / 4 h / 0 °C

3: 84 percent / LiAlH₄ / diethyl ether / 4 h / 20 °C

4: 73 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / 20 °C

With dmap; disodium hydrogenphosphate; lithium aluminium tetrahydride; ethanol; (S)-[1,1']-binaphthalenyl-2,2'-diol; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ja040213e

Reference yield:

: 484061-49-6
tert-butyl (2S,5S,6S)-2-benzyloxymethyl-6-[(1E,3S/R)-3-hydroxynon-1-enyl]-1-azaspiro[4.5]decane-1-carboxylate

: 844698-94-8
tert-butyl (2S,5S,6R)-2-[(benzyloxy)methyl]-6-{(1S,3S)-1-hydroxy-3-[(methylsulfonyl)oxy]nonyl}-1-azaspiro[4.5]decane-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 91 percent / MnO₂ / CH₂Cl₂ / 3 h / 20 °C

2: 92 percent / LiAlH₄; (S)-1,1'-binaphthol; ethanol / tetrahydrofuran / 5 h / -78 °C

3: 68 percent / m-chloroperbenzoic acid; sodium hydrogen phosphate / CH₂Cl₂ / 4 h / 0 °C

4: 84 percent / LiAlH₄ / diethyl ether / 4 h / 20 °C

5: 73 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / 20 °C

With dmap; manganese(IV) oxide; disodium hydrogenphosphate; lithium aluminium tetrahydride; ethanol; (S)-[1,1']-binaphthalenyl-2,2'-diol; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ja040213e