2H-Cyclopenta[b]furan-2-carbonitrile,5-(acetyloxy)hexahydro-,[2R-(2-alpha-,3a-alpha-,5-bta-,6a-alpha-)]-(9CI)

Base Information

• Chemical Name: 2H-Cyclopenta[b]furan-2-carbonitrile,5-(acetyloxy)hexahydro-,[2R-(2-alpha-,3a-alpha-,5-bta-,6a-alpha-)]-(9CI)
• CAS No.: 148217-23-6
• Molecular Formula: C₁₀H₁₃NO₃
• Molecular Weight: 195.218
• Mol file: 148217-23-6.mol

Synonyms:2H-Cyclopenta[b]furan-2-carbonitrile,5-(acetyloxy)hexahydro-,[2R-(2-alpha-,3a-alpha-,5-bta-,6a-alpha-)]-(9CI)

Chemical Property of 2H-Cyclopenta[b]furan-2-carbonitrile,5-(acetyloxy)hexahydro-,[2R-(2-alpha-,3a-alpha-,5-bta-,6a-alpha-)]-(9CI)

Chemical Property:

• PSA: 59.32000
• LogP: 1.00918

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2H-Cyclopenta[b]furan-2-carbonitrile,5-(acetyloxy)hexahydro-,[2R-(2-alpha-,3a-alpha-,5-bta-,6a-alpha-)]-(9CI)

There total 3 articles about 2H-Cyclopenta[b]furan-2-carbonitrile,5-(acetyloxy)hexahydro-,[2R-(2-alpha-,3a-alpha-,5-bta-,6a-alpha-)]-(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:

trimethylsilyl cyanide (7677-24-9) + Acetic acid (3aS,5S,6aS)-2-ethoxy-hexahydro-cyclopenta[b]furan-5-yl ester (148217-21-4) → Acetic acid (2S,3aS,5S,6aS)-2-cyano-hexahydro-cyclopenta[b]furan-5-yl ester (148217-22-5,126261-33-4) + Acetic acid (2R,3aS,5S,6aS)-2-cyano-hexahydro-cyclopenta[b]furan-5-yl ester (148217-23-6,126261-33-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -40 ℃; for 2h; Yield given. Yields of byproduct given;

DOI:10.1021/jm00061a012

Reference yield:

(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate (60410-16-4) → Acetic acid (2R,3aS,5S,6aS)-2-cyano-hexahydro-cyclopenta[b]furan-5-yl ester (148217-23-6,126261-33-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / N-iodosuccinimide / CH₂Cl₂ / 4 h / -20 °C

2: 77 percent / N-Bu₃SnH, AIBN / benzene / 0.5 h / Heating

3: (trimethylsilyl)trifluoromethane sulfonate / CH₂Cl₂ / 2 h / -40 °C

With N-iodo-succinimide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tri-n-butyl-tin hydride; In dichloromethane; benzene;

DOI:10.1021/jm00061a012

Reference yield:

Acetic acid (1R,4S)-4-(1-ethoxy-2-iodo-ethoxy)-cyclopent-2-enyl ester → Acetic acid (2R,3aS,5S,6aS)-2-cyano-hexahydro-cyclopenta[b]furan-5-yl ester (148217-23-6,126261-33-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / N-Bu₃SnH, AIBN / benzene / 0.5 h / Heating

2: (trimethylsilyl)trifluoromethane sulfonate / CH₂Cl₂ / 2 h / -40 °C

With 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tri-n-butyl-tin hydride; In dichloromethane; benzene;

DOI:10.1021/jm00061a012

upstream raw materials:

trimethylsilyl cyanide

Acetic acid (3aS,5S,6aS)-2-ethoxy-hexahydro-cyclopenta[b]furan-5-yl ester

(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate