(3S,5S,6R)-3-[(3R)-4-BroMo-3-hydroxybutyl]-2-oxo-5,6-diphenyl-4-Morpholinecarboxylic Acid tert-Butyl Ester

Base Information

• Chemical Name: (3S,5S,6R)-3-[(3R)-4-BroMo-3-hydroxybutyl]-2-oxo-5,6-diphenyl-4-Morpholinecarboxylic Acid tert-Butyl Ester
• CAS No.: 869111-53-5
• Molecular Formula: C₂₅H₃₀BrNO₅
• Molecular Weight: 504.421
• Mol file: 869111-53-5.mol

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

Chemical Property of (3S,5S,6R)-3-[(3R)-4-BroMo-3-hydroxybutyl]-2-oxo-5,6-diphenyl-4-Morpholinecarboxylic Acid tert-Butyl Ester

Chemical Property:

• Solubility.: Dichloromethane

Purity/Quality:

(3S,5S,6R)-3-[(3R)-4-Bromo-3-hydroxybutyl]-2-oxo-5,6-diphenyl-4-morpholinecarboxylicAcidtert-ButylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (3S,5S,6R)-3-[(3R)-4-Bromo-3-hydroxybutyl]-2-oxo-5,6-diphenyl-4-morpholinecarboxylic Acid tert-Butyl Ester is a reactant used in the preparation of enantiopure stereoisomers of hydroxylysinonorleucine and dihydroxylysinonorleucine (D452900) as reduced collagen cross link.

Technology Process of (3S,5S,6R)-3-[(3R)-4-BroMo-3-hydroxybutyl]-2-oxo-5,6-diphenyl-4-Morpholinecarboxylic Acid tert-Butyl Ester

There total 1 articles about (3S,5S,6R)-3-[(3R)-4-BroMo-3-hydroxybutyl]-2-oxo-5,6-diphenyl-4-Morpholinecarboxylic Acid tert-Butyl Ester 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: 41.0%

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-[(3S)-3-hydroxy-4-bromo-butyl]-2-oxo-5,6-diphenyl-1,4-oxazinane-4-carboxylate (869111-54-6) + 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)

Guidance literature:

With acetic acid; lithium bromide; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1016/j.tetasy.2005.08.023

Reference yield: 92.0%

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)-3,4-epoxybutyl]-2-oxo-5,6-diphenyl-1,4-oxazinane-4-carboxylate (753010-14-9)

Guidance literature:

With CsCO₃; In acetonitrile; at 20 ℃; for 2h;

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

upstream raw materials:

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

Downstream raw materials:

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

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

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

C₅₇H₆₇N₃O₁₀