(3R,5R,6S)-3-((R)-(3-bromo-4-methoxyphenyl)((tert-butyldimethylsilyl)oxy)methyl)-5,6-diphenylmorpholin-2-one

Base Information

• Chemical Name: (3R,5R,6S)-3-((R)-(3-bromo-4-methoxyphenyl)((tert-butyldimethylsilyl)oxy)methyl)-5,6-diphenylmorpholin-2-one
• CAS No.: 1352147-51-3
• Molecular Formula: C₃₀H₃₆BrNO₄Si
• Molecular Weight: 582.61
• Mol file: 1352147-51-3.mol

Synonyms:(3R,5R,6S)-3-((R)-(3-bromo-4-methoxyphenyl)((tert-butyldimethylsilyl)oxy)methyl)-5,6-diphenylmorpholin-2-one

Chemical Property of (3R,5R,6S)-3-((R)-(3-bromo-4-methoxyphenyl)((tert-butyldimethylsilyl)oxy)methyl)-5,6-diphenylmorpholin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5R,6S)-3-((R)-(3-bromo-4-methoxyphenyl)((tert-butyldimethylsilyl)oxy)methyl)-5,6-diphenylmorpholin-2-one

There total 4 articles about (3R,5R,6S)-3-((R)-(3-bromo-4-methoxyphenyl)((tert-butyldimethylsilyl)oxy)methyl)-5,6-diphenylmorpholin-2-one 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: 71.0%

(3R,5R,6S)-benzyl 3-((3-bromo-4-methoxyphenyl)((tert-butyldimethylsilyl) oxy)methyl)-2-oxo5,6-diphenylmorpholine-4-carboxylate (1352147-50-2) → (3R,5R,6S)-3-((R)-(3-bromo-4-methoxyphenyl)((tert-butyldimethylsilyl)oxy)methyl)-5,6-diphenylmorpholin-2-one (1352147-51-3) + (3R,5R,6S)-3-((S)-(3-bromo-4-methoxyphenyl)((tert-butyldimethylsilyl)oxy)methyl)-5,6-diphenylmorpholin-2-one (1352147-49-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; for 7h; under 760.051 Torr; optical yield given as %de;

DOI:10.1016/j.tetlet.2011.11.069

Reference yield:

benzyl (2S,3R)-(+)-6-tert-butyldimethylsilyloxy-2,3-diphenyl-4-morpholin-5-enecarboxylate (911319-41-0) → (3R,5R,6S)-3-((R)-(3-bromo-4-methoxyphenyl)((tert-butyldimethylsilyl)oxy)methyl)-5,6-diphenylmorpholin-2-one (1352147-51-3) + (3R,5R,6S)-3-((S)-(3-bromo-4-methoxyphenyl)((tert-butyldimethylsilyl)oxy)methyl)-5,6-diphenylmorpholin-2-one (1352147-49-9)

Guidance literature:

Multi-step reaction with 2 steps

1: copper(II) bis(trifluoromethanesulfonate) / dichloromethane / 2.5 h / 20 °C

2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 7 h / 760.05 Torr

With palladium 10% on activated carbon; hydrogen; copper(II) bis(trifluoromethanesulfonate); In dichloromethane; ethyl acetate; 1: Mukaiyama aldol reaction;

DOI:10.1016/j.tetlet.2011.11.069

Reference yield:

(5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (105228-46-4,335159-14-3) → (3R,5R,6S)-3-((R)-(3-bromo-4-methoxyphenyl)((tert-butyldimethylsilyl)oxy)methyl)-5,6-diphenylmorpholin-2-one (1352147-51-3) + (3R,5R,6S)-3-((S)-(3-bromo-4-methoxyphenyl)((tert-butyldimethylsilyl)oxy)methyl)-5,6-diphenylmorpholin-2-one (1352147-49-9)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hexamethyldisilazane / tetrahydrofuran / -78 - 20 °C

2: copper(II) bis(trifluoromethanesulfonate) / dichloromethane / 2.5 h / 20 °C

3: palladium 10% on activated carbon; hydrogen / ethyl acetate / 7 h / 760.05 Torr

With palladium 10% on activated carbon; hydrogen; sodium hexamethyldisilazane; copper(II) bis(trifluoromethanesulfonate); In tetrahydrofuran; dichloromethane; ethyl acetate; 2: Mukaiyama aldol reaction;

DOI:10.1016/j.tetlet.2011.11.069

upstream raw materials:

benzyl (2S,3R)-(+)-6-tert-butyldimethylsilyloxy-2,3-diphenyl-4-morpholin-5-enecarboxylate

(3R,5R,6S)-benzyl 3-((3-bromo-4-methoxyphenyl)((tert-butyldimethylsilyl) oxy)methyl)-2-oxo5,6-diphenylmorpholine-4-carboxylate

(5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

tert-butyldimethylsilyl chloride