(2RS,4S,2'R)-2-(2'-tert-butyldimethylsilyloxyoct-7'-en-1'-yl)-2-(phenylsulfanyl)pentan-1,4-olide

Base Information

Chemical Name:(2RS,4S,2'R)-2-(2'-tert-butyldimethylsilyloxyoct-7'-en-1'-yl)-2-(phenylsulfanyl)pentan-1,4-olide
CAS No.:720678-48-8
Molecular Formula:C₂₅H₄₀O₃SSi
Molecular Weight:448.742
Hs Code.:

Synonyms:(2RS,4S,2'R)-2-(2'-tert-butyldimethylsilyloxyoct-7'-en-1'-yl)-2-(phenylsulfanyl)pentan-1,4-olide

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Chemical Property of (2RS,4S,2'R)-2-(2'-tert-butyldimethylsilyloxyoct-7'-en-1'-yl)-2-(phenylsulfanyl)pentan-1,4-olide

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Technology Process of (2RS,4S,2'R)-2-(2'-tert-butyldimethylsilyloxyoct-7'-en-1'-yl)-2-(phenylsulfanyl)pentan-1,4-olide

There total 5 articles about (2RS,4S,2'R)-2-(2'-tert-butyldimethylsilyloxyoct-7'-en-1'-yl)-2-(phenylsulfanyl)pentan-1,4-olide 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: 50.0%

: 184435-75-4
(5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one

: 720678-47-7
(2R)-2-tert-butyldimethylsilyloxy-1-iodooct-7-ene

: 720678-48-8
(2RS,4S,2'R)-2-(2'-tert-butyldimethylsilyloxyoct-7'-en-1'-yl)-2-(phenylsulfanyl)pentan-1,4-olide

Guidance literature:: (5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one; With lithium diisopropyl amide; In tetrahydrofuran; for 0.5h;

(2R)-2-tert-butyldimethylsilyloxy-1-iodooct-7-ene; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; at 20 ℃; for 20h;
DOI:10.1002/chem.200305557

Reference yield:

: 3710-30-3
1,7-Octadiene

: 720678-48-8
(2RS,4S,2'R)-2-(2'-tert-butyldimethylsilyloxyoct-7'-en-1'-yl)-2-(phenylsulfanyl)pentan-1,4-olide

Guidance literature:: Multi-step reaction with 5 steps

1.1: 34 percent / aq. AD-mix-β / 2-methyl-propan-2-ol / 18 h / 0 °C

2.1: 65 percent / 2,4,6-collidine; DMAP / CH₂Cl₂ / 16 h / 0 - 20 °C

3.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 °C

4.1: 95 percent / NaI; NaHCO₃ / acetone / 38 h / Heating

5.1: LDA / tetrahydrofuran / 0.5 h

5.2: 50 percent / HMPA / tetrahydrofuran / 20 h / 20 °C

With 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; dmap; AD-mix-β; sodium hydrogencarbonate; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; acetone; tert-butyl alcohol;
DOI:10.1002/chem.200305557

Reference yield:

: 720678-45-5
(2R)-1-tosyloxyoct-7-en-2-ol

: 720678-48-8
(2RS,4S,2'R)-2-(2'-tert-butyldimethylsilyloxyoct-7'-en-1'-yl)-2-(phenylsulfanyl)pentan-1,4-olide

Guidance literature:: Multi-step reaction with 3 steps

1.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 °C

2.1: 95 percent / NaI; NaHCO₃ / acetone / 38 h / Heating

3.1: LDA / tetrahydrofuran / 0.5 h

3.2: 50 percent / HMPA / tetrahydrofuran / 20 h / 20 °C

With 2,6-dimethylpyridine; sodium hydrogencarbonate; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; acetone;
DOI:10.1002/chem.200305557