D-Lyxonic acid, 2-amino-5-bromo-2,5-dideoxy-, gamma-lactone (9CI)

Base Information

• Chemical Name: D-Lyxonic acid, 2-amino-5-bromo-2,5-dideoxy-, gamma-lactone (9CI)
• CAS No.: 792876-67-6
• Molecular Formula: C₅H₈BrNO₃
• Molecular Weight: 210.027
• Mol file: 792876-67-6.mol

Synonyms:D-Lyxonic acid, 2-amino-5-bromo-2,5-dideoxy-, gamma-lactone (9CI)

Chemical Property of D-Lyxonic acid, 2-amino-5-bromo-2,5-dideoxy-, gamma-lactone (9CI)

Chemical Property:

• PSA: 72.55000
• LogP: -0.30480

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of D-Lyxonic acid, 2-amino-5-bromo-2,5-dideoxy-, gamma-lactone (9CI)

There total 2 articles about D-Lyxonic acid, 2-amino-5-bromo-2,5-dideoxy-, gamma-lactone (9CI) 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:

(2S,3S)-2-tert-Butoxycarbonylamino-3-hydroxy-pent-4-enoic acid (101623-96-5,103366-24-1,105016-01-1,105016-03-3) → (3S,4R,5S)-3-Amino-5-bromomethyl-4-hydroxy-dihydro-furan-2-one (792876-67-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / N-bromosuccinimide / tetrahydrofuran / 0.33 h / 0 °C

2: CF₃COOH

With N-Bromosuccinimide; trifluoroacetic acid; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)95023-8

Reference yield:

((3S,4R,5S)-5-Bromomethyl-4-hydroxy-2-oxo-tetrahydro-furan-3-yl)-carbamic acid tert-butyl ester (105016-02-2) → (3S,4R,5S)-3-Amino-5-bromomethyl-4-hydroxy-dihydro-furan-2-one (792876-67-6)

Guidance literature:

With trifluoroacetic acid;

DOI:10.1016/S0040-4039(00)95023-8

Reference yield:

(3S,4R,5S)-3-Amino-5-bromomethyl-4-hydroxy-dihydro-furan-2-one (792876-67-6) → 2,3-trans-3,4-trans-3,4-dihydroxy-L-proline (74644-88-5,654083-19-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.5N KOH / tetrahydrofuran / 3 h / Ambient temperature

2: Dowex 50Wx₄, 1N NH₃

With potassium hydroxide; ammonium hydroxide; DOWEX 50WX₄; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)95023-8

upstream raw materials:

((3S,4R,5S)-5-Bromomethyl-4-hydroxy-2-oxo-tetrahydro-furan-3-yl)-carbamic acid tert-butyl ester

(2S,3S)-2-tert-Butoxycarbonylamino-3-hydroxy-pent-4-enoic acid

Downstream raw materials:

2,3-trans-3,4-trans-3,4-dihydroxy-L-proline

Refernces