tert-butyl (3S,5S,6R)-3-[(3R)-4-benzylamino-3-hydroxybutyl]-2-oxo-5,6-diphenyl-1,4-oxazinane-4-carboxylate

Base Information

• Chemical Name: tert-butyl (3S,5S,6R)-3-[(3R)-4-benzylamino-3-hydroxybutyl]-2-oxo-5,6-diphenyl-1,4-oxazinane-4-carboxylate
• CAS No.: 869111-57-9
• Molecular Formula: C₃₂H₃₈N₂O₅
• Molecular Weight: 530.664
• Mol file: 869111-57-9.mol

Synonyms:tert-butyl (3S,5S,6R)-3-[(3R)-4-benzylamino-3-hydroxybutyl]-2-oxo-5,6-diphenyl-1,4-oxazinane-4-carboxylate

Chemical Property of tert-butyl (3S,5S,6R)-3-[(3R)-4-benzylamino-3-hydroxybutyl]-2-oxo-5,6-diphenyl-1,4-oxazinane-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (3S,5S,6R)-3-[(3R)-4-benzylamino-3-hydroxybutyl]-2-oxo-5,6-diphenyl-1,4-oxazinane-4-carboxylate

There total 3 articles about tert-butyl (3S,5S,6R)-3-[(3R)-4-benzylamino-3-hydroxybutyl]-2-oxo-5,6-diphenyl-1,4-oxazinane-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: 55.0%

tert-butyl (3S,5S,6R)-3-[(3R)-3,4-epoxybutyl]-2-oxo-5,6-diphenyl-1,4-oxazinane-4-carboxylate (753010-14-9) + benzylamine (100-46-9) → tert-butyl (3S,5S,6R)-3-[(3R)-4-benzylamino-3-hydroxybutyl]-2-oxo-5,6-diphenyl-1,4-oxazinane-4-carboxylate (869111-57-9)

Guidance literature:

With lithium perchlorate; In acetonitrile; at 60 ℃; for 3h;

DOI:10.1016/j.tetasy.2005.08.023

Reference yield:

tert-butyl (3S,5S,6R)-3-[(3R)-3-hydroxy-4-bromo-butyl]-2-oxo-5,6-diphenyl-1,4-oxazinane-4-carboxylate (869111-53-5) → tert-butyl (3S,5S,6R)-3-[(3R)-4-benzylamino-3-hydroxybutyl]-2-oxo-5,6-diphenyl-1,4-oxazinane-4-carboxylate (869111-57-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / CsCO₃ / acetonitrile / 2 h / 20 °C

2: 55 percent / lithium perchlorate / acetonitrile / 3 h / 60 °C

With lithium perchlorate; In acetonitrile;

DOI:10.1016/j.tetasy.2005.08.023

Reference yield:

tert-butyl (3S,5S,6R)-3-(2-((RS)oxiran-2-yl)ethyl)-2-oxo-5,6-diphenylmorpholine-4-carboxylate (937183-38-5) → tert-butyl (3S,5S,6R)-3-[(3R)-4-benzylamino-3-hydroxybutyl]-2-oxo-5,6-diphenyl-1,4-oxazinane-4-carboxylate (869111-57-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 41 percent / anhydrous lithium bromide; AcOH / tetrahydrofuran / 4 h / 20 °C

2: 92 percent / CsCO₃ / acetonitrile / 2 h / 20 °C

3: 55 percent / lithium perchlorate / acetonitrile / 3 h / 60 °C

With lithium perchlorate; acetic acid; lithium bromide; In tetrahydrofuran; acetonitrile;

DOI:10.1016/j.tetasy.2005.08.023

upstream raw materials:

tert-butyl (3S,5S,6R)-3-[(3R)-3,4-epoxybutyl]-2-oxo-5,6-diphenyl-1,4-oxazinane-4-carboxylate

benzylamine

tert-butyl (3S,5S,6R)-3-[(3R)-3-hydroxy-4-bromo-butyl]-2-oxo-5,6-diphenyl-1,4-oxazinane-4-carboxylate

tert-butyl (3S,5S,6R)-3-(2-((RS)oxiran-2-yl)ethyl)-2-oxo-5,6-diphenylmorpholine-4-carboxylate

Downstream raw materials:

C₅₇H₆₇N₃O₁₀

(2S,5R)-2-amino-6[(2S,5S)-5-amino-5-carboxy-2-hydroxypentylamino]-5-hydroxyhexanoic acid