(2S,3R,4S)-6-acetamido-4-(tert-butyldiphenylsilyloxy)-2,3-epoxycyclohex-5-enone

Base Information

• Chemical Name: (2S,3R,4S)-6-acetamido-4-(tert-butyldiphenylsilyloxy)-2,3-epoxycyclohex-5-enone
• CAS No.: 174591-72-1
• Molecular Formula: C₂₄H₂₇NO₄Si
• Molecular Weight: 421.568
• Mol file: 174591-72-1.mol

Synonyms:(2S,3R,4S)-6-acetamido-4-(tert-butyldiphenylsilyloxy)-2,3-epoxycyclohex-5-enone

Chemical Property of (2S,3R,4S)-6-acetamido-4-(tert-butyldiphenylsilyloxy)-2,3-epoxycyclohex-5-enone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S)-6-acetamido-4-(tert-butyldiphenylsilyloxy)-2,3-epoxycyclohex-5-enone

There total 4 articles about (2S,3R,4S)-6-acetamido-4-(tert-butyldiphenylsilyloxy)-2,3-epoxycyclohex-5-enone 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: 77.0%

(2S,3R,4S)-6--4-(tert-butyldiphenylsilyloxy)-2,3-epoxycyclohex-5-enone (174591-71-0) → (2S,3R,4S)-6-acetamido-4-(tert-butyldiphenylsilyloxy)-2,3-epoxycyclohex-5-enone (174591-72-1)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; tri-n-butyl-tin hydride; acetic acid; In dichloromethane; at -20 ℃; for 1h;

DOI:10.1055/s-1995-4141

Reference yield:

(2R,4R,7S,8R)-11-<(allyloxycarbonyl)amino>-7,8-epoxy-2,4-dimethyl-1,5-dioxaspiro<5.5>non-10-en-9-one (174531-88-5) → (2S,3R,4S)-6-acetamido-4-(tert-butyldiphenylsilyloxy)-2,3-epoxycyclohex-5-enone (174591-72-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaBH₄, 2.) imidazole / 1.) CH₃OH, -20 deg C, 30 min, 2.) CH₂Cl₂, 21 deg C, 4 h

2: 78 percent / PPTS, TsH*H₂O / acetone; H₂O / 48 h / 38 °C

3: 54 percent / DMAP / CH₂Cl₂ / 8 h / -20 °C

4: 77 percent / AcOH, Bu₃SnH, PdCl₂(PPh₃)2 / CH₂Cl₂ / 1 h / -20 °C

With 1H-imidazole; dmap; bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; TsH*H₂O; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; acetic acid; In dichloromethane; water; acetone;

DOI:10.1055/s-1995-4141

Reference yield:

(2S,3R,4S)-6-<(allyloxycarbonyl)amino>-4-(tert-butyldiphenylsilyloxy)-2,3-epoxycyclohex-5-enone (174591-70-9) → (2S,3R,4S)-6-acetamido-4-(tert-butyldiphenylsilyloxy)-2,3-epoxycyclohex-5-enone (174591-72-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / DMAP / CH₂Cl₂ / 8 h / -20 °C

2: 77 percent / AcOH, Bu₃SnH, PdCl₂(PPh₃)2 / CH₂Cl₂ / 1 h / -20 °C

With dmap; bis-triphenylphosphine-palladium(II) chloride; tri-n-butyl-tin hydride; acetic acid; In dichloromethane;

DOI:10.1055/s-1995-4141

upstream raw materials:

(2S,3R,4S)-6--4-(tert-butyldiphenylsilyloxy)-2,3-epoxycyclohex-5-enone

(2R,4R,7S,8R)-11-<(allyloxycarbonyl)amino>-7,8-epoxy-2,4-dimethyl-1,5-dioxaspiro<5.5>non-10-en-9-one

(2S,3R,4S)-6-<(allyloxycarbonyl)amino>-4-(tert-butyldiphenylsilyloxy)-2,3-epoxycyclohex-5-enone

(2R,4R,7S,8R,9S)-11-<(allyloxycarbonyl)amino>-9-(tert-butyldiphenylsilyloxy)-7,8-epoxy-2,4-dimethyl-1,5-dioxaspiro<5.5>non-10-ene

Downstream raw materials:

LL-C10037α