(2S,5S,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((E)-non-2-enoyl)-1-aza-spiro[4.5]decane-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2S,5S,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((E)-non-2-enoyl)-1-aza-spiro[4.5]decane-1-carboxylic acid tert-butyl ester
CAS No.:791635-35-3
Molecular Formula:C₄₀H₅₉NO₄Si
Molecular Weight:645.998
Hs Code.:

Synonyms:(2S,5S,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((E)-non-2-enoyl)-1-aza-spiro[4.5]decane-1-carboxylic acid tert-butyl ester

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Chemical Property of (2S,5S,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((E)-non-2-enoyl)-1-aza-spiro[4.5]decane-1-carboxylic acid tert-butyl ester

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Technology Process of (2S,5S,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((E)-non-2-enoyl)-1-aza-spiro[4.5]decane-1-carboxylic acid tert-butyl ester

There total 10 articles about (2S,5S,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((E)-non-2-enoyl)-1-aza-spiro[4.5]decane-1-carboxylic acid tert-butyl ester 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: 90.0%

: 791635-33-1
(2S,5S,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((E)-1-hydroxy-non-2-enyl)-1-aza-spiro[4.5]decane-1-carboxylic acid tert-butyl ester

: 791635-35-3
(2S,5S,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((E)-non-2-enoyl)-1-aza-spiro[4.5]decane-1-carboxylic acid tert-butyl ester

Guidance literature:: With manganese(IV) oxide; In dichloromethane; at 20 ℃; for 48h;
DOI:10.1021/ol048353g DOI:10.1021/jo0501846

Reference yield:

: 138629-30-8,138871-56-4
(S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate

: 791635-35-3
(2S,5S,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((E)-non-2-enoyl)-1-aza-spiro[4.5]decane-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: t-BuLi / diethyl ether / 1 h / -78 °C

1.2: 61 percent / tetrahydrofuran; diethyl ether / 2 h / -78 °C

2.1: 71 percent / tetrahydrofuran; toluene / 3 h / -10 °C

3.1: 90 percent / K₂CO₃ / methanol; H₂O / 0 - 20 °C

4.1: 94 percent / m-CPBA / CH₂Cl₂ / -10 - 20 °C

5.1: 80 percent / Et₃N; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / -10 - 20 °C

6.1: 66 percent / NH₂NH₂; AcOH / methanol / -10 - 20 °C

7.1: 90 percent / MnO₂ / CH₂Cl₂ / 48 h / 20 °C

With manganese(IV) oxide; pyridine-SO₃ complex; tert.-butyl lithium; potassium carbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; hydrazine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; toluene; 2.1: Prins cyclization / 6.1: Wharton rearrangement;
DOI:10.1021/jo0501846

Reference yield:

: 791635-28-4
(2S,5S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((E)-3-formyloxy-non-1-enyl)-1-aza-spiro[4.5]decane-1-carboxylic acid tert-butyl ester

: 791635-35-3
(2S,5S,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((E)-non-2-enoyl)-1-aza-spiro[4.5]decane-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / K₂CO₃ / methanol; H₂O / 0 - 20 °C

2: 94 percent / m-CPBA / CH₂Cl₂ / -10 - 20 °C

3: 80 percent / Et₃N; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / -10 - 20 °C

4: 66 percent / NH₂NH₂; AcOH / methanol / -10 - 20 °C

5: 90 percent / MnO₂ / CH₂Cl₂ / 48 h / 20 °C

With manganese(IV) oxide; pyridine-SO₃ complex; potassium carbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; hydrazine; In methanol; dichloromethane; water; dimethyl sulfoxide; 4: Wharton rearrangement;
DOI:10.1021/jo0501846