S-ethyl (2S,3R,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-6-methyl-2-[(phenyl)methoxy]hept-4-enethioate

Base Information

• Chemical Name: S-ethyl (2S,3R,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-6-methyl-2-[(phenyl)methoxy]hept-4-enethioate
• CAS No.: 442913-41-9
• Molecular Formula: C₂₃H₃₈O₃SSi
• Molecular Weight: 422.704
• Mol file: 442913-41-9.mol

Synonyms:S-ethyl (2S,3R,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-6-methyl-2-[(phenyl)methoxy]hept-4-enethioate

Chemical Property of S-ethyl (2S,3R,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-6-methyl-2-[(phenyl)methoxy]hept-4-enethioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of S-ethyl (2S,3R,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-6-methyl-2-[(phenyl)methoxy]hept-4-enethioate

There total 6 articles about S-ethyl (2S,3R,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-6-methyl-2-[(phenyl)methoxy]hept-4-enethioate 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: 95.0%

lithium thioethoxide (30383-01-8) + (1S,4S)-2-{(2S,3R,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-6-methyl-2-[(phenyl)methoxy]hept-4-enoyl}-4,5,5-trimethyl-2-azabicyclo[2.2.1]heptan-3-one (442913-26-0) → S-ethyl (2S,3R,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-6-methyl-2-[(phenyl)methoxy]hept-4-enethioate (442913-41-9)

Guidance literature:

In tetrahydrofuran; at -78 - -40 ℃;

DOI:10.1021/ol026101e

Reference yield:

(E)-4-methylpent-2-enal (24502-08-7) → S-ethyl (2S,3R,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-6-methyl-2-[(phenyl)methoxy]hept-4-enethioate (442913-41-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: DIPEA; diethylboron triflate / CH₂Cl₂ / 1 h / -78 °C

1.2: 85 percent / CH₂Cl₂ / 9 h / -50 °C

2.1: 94 percent / imidazole / dimethylformamide / 13 h / 20 °C

3.1: BiLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

3.2: 93 percent / tetrahydrofuran; hexane / 5 h / -40 °C

With 1H-imidazole; n-butyllithium; N-ethyl-N,N-diisopropylamine; diethylboron trifluoromethanesulfonate; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/hlca.200290026

Reference yield:

(1S,4S)-4,5,5-trimethyl-{[(phenyl)methoxy]acetyl}-2-azabicyclo[2.2.1]heptan-3-one (442913-24-8) → S-ethyl (2S,3R,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-6-methyl-2-[(phenyl)methoxy]hept-4-enethioate (442913-41-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: DIPEA; diethylboron triflate / CH₂Cl₂ / 1 h / -78 °C

1.2: 85 percent / CH₂Cl₂ / 9 h / -50 °C

2.1: 94 percent / imidazole / dimethylformamide / 13 h / 20 °C

3.1: BiLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

3.2: 93 percent / tetrahydrofuran; hexane / 5 h / -40 °C

With 1H-imidazole; n-butyllithium; N-ethyl-N,N-diisopropylamine; diethylboron trifluoromethanesulfonate; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/hlca.200290026

upstream raw materials:

lithium thioethoxide

(1S,4S)-2-{(2S,3R,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-6-methyl-2-[(phenyl)methoxy]hept-4-enoyl}-4,5,5-trimethyl-2-azabicyclo[2.2.1]heptan-3-one

(E)-4-methylpent-2-enal

Benzyloxyacetyl chloride

Downstream raw materials:

S-phenyl (2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-[(phenyl)methoxy]non-6-enethioate

(2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-N-[(3S)-2,3,4,5,6,7-hexahydro-2-oxoazepin-3-yl]-3-hydroxy-2-methoxy-8-methyl-4-[(phenyl)methoxy]non-6-enamide

(3S,6S)-6-[((2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-(phenylmethoxy)non-6-enoyl)amino]-2,3,4,5,6,7-hexahydro-1-methyl-7-oxoazepin-3-yl acetate

(2S,3R,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-6-methyl-2-[(phenyl)methoxy]hept-4-enal