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

Base Information

• Chemical Name: methyl (2S,4R)-1-[(E)-6-tert-butyldiphenylsilyloxy-2-methylhex-2-enyl]-4-(methoxymethyloxy)-pyrrolidine-2-carboxylate
• CAS No.: 1380511-81-8
• Molecular Formula: C₃₁H₄₅NO₅Si
• Molecular Weight: 539.788

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

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

Chemical Property:

Purity/Quality:

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

There total 6 articles about methyl (2S,4R)-1-[(E)-6-tert-butyldiphenylsilyloxy-2-methylhex-2-enyl]-4-(methoxymethyloxy)-pyrrolidine-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: 73.0%

methyl (2S,4R)-1-[(E)-6-tert-butyldiphenylsilyloxy-2-methylhex-2-enyl]-4-hydroxypyrrolidine-2-carboxylate (1380511-79-4) + chloromethyl methyl ether (107-30-2) → methyl (2S,4R)-1-[(E)-6-tert-butyldiphenylsilyloxy-2-methylhex-2-enyl]-4-(methoxymethyloxy)-pyrrolidine-2-carboxylate (1380511-81-8)

Guidance literature:

methyl (2S,4R)-1-[(E)-6-tert-butyldiphenylsilyloxy-2-methylhex-2-enyl]-4-hydroxypyrrolidine-2-carboxylate; chloromethyl methyl ether; With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 168h; Inert atmosphere; Reflux;

With sodium carbonate; In dichloromethane; water; for 3h; Inert atmosphere;

DOI:10.1002/ejoc.201200073

Reference yield:

C24H34O4SSi → methyl (2S,4R)-1-[(E)-6-tert-butyldiphenylsilyloxy-2-methylhex-2-enyl]-4-(methoxymethyloxy)-pyrrolidine-2-carboxylate (1380511-81-8)

Guidance literature:

Multi-step reaction with 2 steps

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

2.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 168 h / 0 - 20 °C / Inert atmosphere; Reflux

2.2: 3 h / Inert atmosphere

With dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1002/ejoc.201200073

Reference yield:

4-((tert-butyldiphenylsilyl)oxy)butanal (127793-62-8) → methyl (2S,4R)-1-[(E)-6-tert-butyldiphenylsilyloxy-2-methylhex-2-enyl]-4-(methoxymethyloxy)-pyrrolidine-2-carboxylate (1380511-81-8)

Guidance literature:

Multi-step reaction with 4 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

4.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 168 h / 0 - 20 °C / Inert atmosphere; Reflux

4.2: 3 h / Inert atmosphere

With pyridine; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; bromine; magnesium; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1002/ejoc.201200073

upstream raw materials:

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

chloromethyl methyl ether

4-((tert-butyldiphenylsilyl)oxy)butanal

4-(tret-butyldiphenylsilyloxy)butan-1-ol

Downstream raw materials:

anti-(2S,3S)-2-[E-2-(2-bromo-5-methoxyphenyl)ethenyl]-3-(3-tert-butyldiphenylsilyloxypropyl)-1-[(2S,4R)-2-(methoxymethoxymethyl)-4-methoxymethyloxy-pyrrolidin-1-yl]-4-methyl-4-pentene-1-one

anti-(2R,3R)-2-[E-2-(2-bromo-5-methoxyphenyl)ethenyl]-3-(3-tert-butyldiphenylsilyloxypropyl)-1-[(2S,4R)-2-(methoxymethoxymethyl)-4-methoxymethyloxy-pyrrolidin-1-yl]-4-methyl-4-pentene-1-one

anti-(2R,3R)-2-[E-2-(2-bromo-5-methoxyphenyl)-ethenyl]-1-[(2S,4R)-2-(tert-butyldiphenylsilyloxymethyl)-4-methoxymethyloxy-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-4-methyl-4-pentene-1-one

anti-(2S,3S)-2-[E-2-(2-bromo-5-methoxyphenyl)-ethenyl]-1-[(2S,4R)-2-(tert-butyldiphenylsilyloxymethyl)-4-methoxymethyloxy-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-4-methyl-4-pentene-1-one

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