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

Base Information

• Chemical Name: (3R,5R,6S)-benzyl 3-((3-bromo-4-methoxyphenyl)((tert-butyldimethylsilyl) oxy)methyl)-2-oxo5,6-diphenylmorpholine-4-carboxylate
• CAS No.: 1352147-50-2
• Molecular Formula: C₃₈H₄₂BrNO₆Si
• Molecular Weight: 716.744
• Mol file: 1352147-50-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (3R,5R,6S)-benzyl 3-((3-bromo-4-methoxyphenyl)((tert-butyldimethylsilyl) oxy)methyl)-2-oxo5,6-diphenylmorpholine-4-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: 99.0%

benzyl (2S,3R)-(+)-6-tert-butyldimethylsilyloxy-2,3-diphenyl-4-morpholin-5-enecarboxylate (911319-41-0) + 3-bromo-4-methoxybenzylaldehyde (34841-06-0) → (3R,5R,6S)-benzyl 3-((3-bromo-4-methoxyphenyl)((tert-butyldimethylsilyl) oxy)methyl)-2-oxo5,6-diphenylmorpholine-4-carboxylate (1352147-50-2)

Guidance literature:

With copper(II) bis(trifluoromethanesulfonate); In dichloromethane; at 20 ℃; for 2.5h; diastereoselective 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)-benzyl 3-((3-bromo-4-methoxyphenyl)((tert-butyldimethylsilyl) oxy)methyl)-2-oxo5,6-diphenylmorpholine-4-carboxylate (1352147-50-2)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With sodium hexamethyldisilazane; copper(II) bis(trifluoromethanesulfonate); In tetrahydrofuran; dichloromethane; 2: Mukaiyama aldol reaction;

DOI:10.1016/j.tetlet.2011.11.069

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (3R,5R,6S)-benzyl 3-((3-bromo-4-methoxyphenyl)((tert-butyldimethylsilyl) oxy)methyl)-2-oxo5,6-diphenylmorpholine-4-carboxylate (1352147-50-2)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With sodium hexamethyldisilazane; copper(II) bis(trifluoromethanesulfonate); In tetrahydrofuran; dichloromethane; 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

3-bromo-4-methoxybenzylaldehyde

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

tert-butyldimethylsilyl chloride

Downstream raw materials:

(2R,3S)-methyl 3-(3-bromo-4-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)-2-(((1R,2S)-2-hydroxy 1,2diphenylethyl)(methyl)amino)propanoate

(2R,3S)-methyl 3-(3-bromo-4-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)-2-(methylamino)propanoate

(2R,3S)-methyl 2-amino-3-(3-bromo-4-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)propanoate

(2R,3S)-methyl 2-amino-3-(3-bromo-4-methoxyphenyl)-3-hydroxypropanoate