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

Base Information

• Chemical Name: benzyl (2S,3R)-(+)-6-tert-butyldimethylsilyloxy-2,3-diphenyl-4-morpholin-5-enecarboxylate
• CAS No.: 911319-41-0
• Molecular Formula: C₃₀H₃₅NO₄Si
• Molecular Weight: 501.698
• Mol file: 911319-41-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about benzyl (2S,3R)-(+)-6-tert-butyldimethylsilyloxy-2,3-diphenyl-4-morpholin-5-enecarboxylate 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: 97.0%

(5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (105228-46-4,335159-14-3) + tert-butyldimethylsilyl chloride (18162-48-6) → benzyl (2S,3R)-(+)-6-tert-butyldimethylsilyloxy-2,3-diphenyl-4-morpholin-5-enecarboxylate (911319-41-0)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 - 25 ℃;

DOI:10.1021/ol061524s

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: 76.0%

benzyl (2S,3R)-(+)-6-tert-butyldimethylsilyloxy-2,3-diphenyl-4-morpholin-5-enecarboxylate (911319-41-0) + 6-methoxyquinoline-4-carbaldehyde (4363-94-4) → benzyl (2S,3R)-5-[hydroxy-4-[6-methoxyquinolyl]methyl]-6-oxo-2,3-diphenyl-4-morpholinecarboxylate + (3R,5R,6S)-3-[(R)-Hydroxy-(6-methoxy-quinolin-4-yl)-methyl]-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester (911319-42-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1021/ol061524s

upstream raw materials:

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

tert-butyldimethylsilyl chloride

Downstream raw materials:

(3R,5R,6S)-3-[(R)-Hydroxy-(6-methoxy-quinolin-4-yl)-methyl]-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

(3R,5R,6S)-3-[(R)-(6-Methoxy-quinolin-4-yl)-triethylsilanyloxy-methyl]-5,6-diphenyl-morpholin-2-one

(2R,3R)-2-((1R,2S)-2-Hydroxy-1,2-diphenyl-ethylamino)-3-(6-methoxy-quinolin-4-yl)-3-triethylsilanyloxy-propionic acid methyl ester

(3R,5R,6S)-3-[(R)-(6-Methoxy-quinolin-4-yl)-triethylsilanyloxy-methyl]-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester