trans-(-)-(3S,4S)-4-benzyl-5-oxo-3-tetrahydrofurancarboxylic acid

Base Information

• Chemical Name: trans-(-)-(3S,4S)-4-benzyl-5-oxo-3-tetrahydrofurancarboxylic acid
• CAS No.: 1155859-90-7
• Molecular Formula: C₁₂H₁₂O₄
• Molecular Weight: 220.225
• Mol file: 1155859-90-7.mol

Synonyms:

Chemical Property of trans-(-)-(3S,4S)-4-benzyl-5-oxo-3-tetrahydrofurancarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-(-)-(3S,4S)-4-benzyl-5-oxo-3-tetrahydrofurancarboxylic acid

There total 3 articles about trans-(-)-(3S,4S)-4-benzyl-5-oxo-3-tetrahydrofurancarboxylic acid 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: 40.0%

ethyl trans-4-benzyl-5-oxo-3-tetrahydrofurancarboxylate → trans-(-)-(3S,4S)-4-benzyl-5-oxo-3-tetrahydrofurancarboxylic acid (1155859-90-7) + trans-(+)-(3R,4R)-4-benzyl-5-oxo-3-tetrahydrofurancarboxylic acid + ethyl trans-(+)-(3R,4R)-4-benzyl-5-oxo-3-tetrahydrofurancarboxylate (1155859-92-9)

Guidance literature:

ethyl trans-4-benzyl-5-oxo-3-tetrahydrofurancarboxylate; With sodium hydroxide; α-chymotrypsin; In water; for 8.5h; pH=7.4; aq. phosphate buffer; Enzymatic reaction;

With hydrogenchloride; water; pH=2; optical yield given as %ee; regioselective reaction;

DOI:10.1016/j.tetasy.2009.01.027

Reference yield: 13.0%

ethyl trans-4-benzyl-5-oxo-3-tetrahydrofurancarboxylate → trans-(-)-(3S,4S)-4-benzyl-5-oxo-3-tetrahydrofurancarboxylic acid (1155859-90-7) + ethyl trans-(-)-(3S,4S)-4-benzyl-5-oxo-3-tetrahydrofurancarboxylate + ethyl trans-(+)-(3R,4R)-4-benzyl-5-oxo-3-tetrahydrofurancarboxylate (1155859-92-9)

Guidance literature:

ethyl trans-4-benzyl-5-oxo-3-tetrahydrofurancarboxylate; With sodium hydroxide; α-chymotrypsin; In water; at 20 ℃; for 0.933333h; pH=7.4; aq. phosphate buffer; Enzymatic reaction;

With hydrogenchloride; water; pH=2; optical yield given as %ee; regioselective reaction;

DOI:10.1016/j.tetasy.2009.01.027

Reference yield:

ethyl cis-4-benzyl-5-oxo-3-tetrahydrofurancarboxylate → trans-(-)-(3S,4S)-4-benzyl-5-oxo-3-tetrahydrofurancarboxylic acid (1155859-90-7) + trans-(+)-(3R,4R)-4-benzyl-5-oxo-3-tetrahydrofurancarboxylic acid + ethyl trans-(-)-(3S,4S)-4-benzyl-5-oxo-3-tetrahydrofurancarboxylate + ethyl trans-(+)-(3R,4R)-4-benzyl-5-oxo-3-tetrahydrofurancarboxylate (1155859-92-9)

Guidance literature:

ethyl cis-4-benzyl-5-oxo-3-tetrahydrofurancarboxylate; With Candida cylindracea lipase; sodium hydroxide; In water; at 20 ℃; for 1.3h; pH=7.4; aq. phosphate buffer; Enzymatic reaction;

With hydrogenchloride; water; pH=2; optical yield given as %ee; regioselective reaction;

DOI:10.1016/j.tetasy.2009.01.027

Downstream raw materials:

(1'S,3S,4S)-1-(9-anthryl)-2,2,2-trifluoroethyl-4-benzyl-5-oxo-3-tetrahydrofurancarboxylate

(1'R,3S,4S)-1-(9-anthryl)-2,2,2-trifluoroethyl-4-benzyl-5-oxo-3-tetrahydrofurancarboxylate