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

Base Information

• Chemical Name: 2R-(2-acetoxyethyl)-3-cyclopenten-1S-ol
• CAS No.: 54442-06-7
• Molecular Formula: C₉H₁₄O₃
• Molecular Weight: 170.208
• Mol file: 54442-06-7.mol

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

Chemical Property of 2R-(2-acetoxyethyl)-3-cyclopenten-1S-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2R-(2-acetoxyethyl)-3-cyclopenten-1S-ol

There total 1 articles about 2R-(2-acetoxyethyl)-3-cyclopenten-1S-ol 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:

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one (26054-46-6) → 2R-(2-acetoxyethyl)-3-cyclopenten-1S-ol (54442-06-7)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With 2,4,6-trimethyl-pyridine; lithium aluminium tetrahydride; In diethyl ether; dichloromethane;

DOI:10.1021/jm1012787

Reference yield:

2R-(2-acetoxyethyl)-3-cyclopenten-1S-ol (54442-06-7) → (3aS,4S,7aR)-hexahydro-4H-furo[2,3-b]pyran-4-yl (4-nitrophenyl) carbonate (1075209-47-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

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

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

3.2: 2 h / 0 °C / Inert atmosphere

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

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

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

With pyridine; 2,6-dimethylpyridine; triethylsilane; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; potassium carbonate; ozone; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm1012787

Reference yield:

2R-(2-acetoxyethyl)-3-cyclopenten-1S-ol (54442-06-7) → GRL-0476 (1075209-49-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

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

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

3.2: 2 h / 0 °C / Inert atmosphere

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

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

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

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

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

DOI:10.1021/jm1012787

upstream raw materials:

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one

Downstream raw materials:

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

GRL-0476

(3aS,4S,7aR)-hexahydro-2H-furo[2,3-b]pyran-4-yl-(2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl carbamate

(3aS,4S,7aR)-hexahydro-2H-furo[2,3-b]pyran-4-yl-(2S,3R)-3-hydroxy-4-(4-(hydroxymethyl)-N-isobutylphenylsulfonamido)-1-phenylbutan-2-yl carbamate

Refernces

• 1、 Ghosh, Arun K.,Chapsal, Bruno D.,Baldridge, Abigail,Steffey, Melinda P.,Walters, D. Eric,Koh, Yasuhiro,Amano, Masayuki,Mitsuya, Hiroaki. "Design and synthesis of potent HIV-1 protease inhibitors incorporating hexahydrofuropyranol-derived high affinity P2 ligands: Structure-activity studies and biological evaluation". . p. 622 - 634. Retrieved 2011/03/21.