methyl (2S,4R)-1-[(E)-6-tert-butyldiphenylsilyloxy-2-methylhex-2-enyl]-4-hydroxypyrrolidine-2-carboxylate

Base Information

Chemical Name:methyl (2S,4R)-1-[(E)-6-tert-butyldiphenylsilyloxy-2-methylhex-2-enyl]-4-hydroxypyrrolidine-2-carboxylate
CAS No.:1380511-79-4
Molecular Formula:C₂₉H₄₁NO₄Si
Molecular Weight:495.734
Hs Code.:

Synonyms:methyl (2S,4R)-1-[(E)-6-tert-butyldiphenylsilyloxy-2-methylhex-2-enyl]-4-hydroxypyrrolidine-2-carboxylate

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Chemical Property of methyl (2S,4R)-1-[(E)-6-tert-butyldiphenylsilyloxy-2-methylhex-2-enyl]-4-hydroxypyrrolidine-2-carboxylate

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Technology Process of methyl (2S,4R)-1-[(E)-6-tert-butyldiphenylsilyloxy-2-methylhex-2-enyl]-4-hydroxypyrrolidine-2-carboxylate

There total 5 articles about methyl (2S,4R)-1-[(E)-6-tert-butyldiphenylsilyloxy-2-methylhex-2-enyl]-4-hydroxypyrrolidine-2-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:

: C₂₄H₃₄O₄SSi

: 40216-83-9
L-4-hydroxyproline methyl ester hydrochloride

: 1380511-79-4
methyl (2S,4R)-1-[(E)-6-tert-butyldiphenylsilyloxy-2-methylhex-2-enyl]-4-hydroxypyrrolidine-2-carboxylate

Guidance literature:: With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triethylamine; triphenylphosphine; In tetrahydrofuran; acetonitrile; at 20 ℃; for 24h; Inert atmosphere;
DOI:10.1002/ejoc.201200073

Reference yield:

: 127793-62-8
4-((tert-butyldiphenylsilyl)oxy)butanal

: 1380511-79-4
methyl (2S,4R)-1-[(E)-6-tert-butyldiphenylsilyloxy-2-methylhex-2-enyl]-4-hydroxypyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: bromine; magnesium / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

1.3: 0 °C

2.1: pyridine; N-ethyl-N,N-diisopropylamine / dichloromethane; acetonitrile / 3 h / -15 - 20 °C / Inert atmosphere

3.1: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triethylamine; triphenylphosphine / tetrahydrofuran; acetonitrile / 24 h / 20 °C / Inert atmosphere

With pyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; bromine; magnesium; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1002/ejoc.201200073

Reference yield:

: 130372-07-5
4-(tret-butyldiphenylsilyloxy)butan-1-ol

: 1380511-79-4
methyl (2S,4R)-1-[(E)-6-tert-butyldiphenylsilyloxy-2-methylhex-2-enyl]-4-hydroxypyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide / dichloromethane; water / Inert atmosphere; Cooling with ice

2.1: bromine; magnesium / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

2.3: 0 °C

3.1: pyridine; N-ethyl-N,N-diisopropylamine / dichloromethane; acetonitrile / 3 h / -15 - 20 °C / Inert atmosphere

4.1: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triethylamine; triphenylphosphine / tetrahydrofuran; acetonitrile / 24 h / 20 °C / Inert atmosphere

With pyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; bromine; sodium hydrogencarbonate; magnesium; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; potassium bromide; In tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1002/ejoc.201200073