GRL-0476

Base Information

• Chemical Name: GRL-0476
• CAS No.: 1075209-49-2
• Molecular Formula: C₂₉H₄₀N₂O₈S
• Molecular Weight: 576.711
• Mol file: 1075209-49-2.mol

Synonyms:GRL-0476

Chemical Property of GRL-0476

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of GRL-0476

There total 15 articles about GRL-0476 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: 76.0%

(3aS,4S,7aR)-hexahydro-4H-furo[2,3-b]pyran-4-yl (4-nitrophenyl) carbonate (1075209-47-0) + N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-methoxybenzenesulfonamide (159005-71-7) → GRL-0476 (1075209-49-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 - 23 ℃; for 120h; Inert atmosphere;

DOI:10.1021/acs.joc.9b01361

Reference yield: 55.0%

(3aS,4S,7aR)-hexahydro-4H-furo[2,3-b]pyran-4-yl (4-nitrophenyl) carbonate (1075209-47-0) + tert-butyl (1S,2R)-1-benzyl-2-hydroxy-3-{isobutyl[(4-methoxyphenyl)sulfonyl]amino}propylcarbamate (159006-03-8) → GRL-0476 (1075209-49-2)

Guidance literature:

tert-butyl (1S,2R)-1-benzyl-2-hydroxy-3-{isobutyl[(4-methoxyphenyl)sulfonyl]amino}propylcarbamate; With trifluoroacetic acid; In dichloromethane; at 23 ℃; for 2h;

(3aS,4S,7aR)-hexahydro-4H-furo[2,3-b]pyran-4-yl (4-nitrophenyl) carbonate; With triethylamine; In dichloromethane; at 0 - 23 ℃; Inert atmosphere;

Reference yield:

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one (26054-46-6) → GRL-0476 (1075209-49-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: lithium aluminium tetrahydride / diethyl ether / 1.5 h / 0 °C / Inert atmosphere

2.1: 2,4,6-trimethyl-pyridine / dichloromethane / 7 h / -78 °C / Inert atmosphere

3.1: 2,6-dimethylpyridine / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

4.1: potassium carbonate / methanol / 2 h / 23 °C

5.1: ozone / dichloromethane / 0.08 h / -78 °C / Inert atmosphere

5.2: 2 h / 0 °C / Inert atmosphere

6.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 23 °C

8.1: pyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

9.1: triethylamine / acetonitrile / 0 - 23 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; triethylsilane; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; potassium carbonate; ozone; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1021/jm1012787

upstream raw materials:

2R-(2-acetoxyethyl)-3-cyclopenten-1S-ol

(1S,2R)-2-[1-(tert-butyldimethylsilyloxy)cyclopent-3-en-2-yl]ethyl acetate

(3aS,4S,7aR)-hexahydro-4H-furo[2,3-b]pyran-4-yl (4-nitrophenyl) carbonate

N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-methoxybenzenesulfonamide