Benzoic acid (Z)-(R)-1-{(E)-2-[(2R,3S)-3-(3,4-dimethoxy-benzyloxy)-5-methoxy-tetrahydro-furan-2-yl]-vinyl}-non-3-enyl ester

Base Information

• Chemical Name: Benzoic acid (Z)-(R)-1-{(E)-2-[(2R,3S)-3-(3,4-dimethoxy-benzyloxy)-5-methoxy-tetrahydro-furan-2-yl]-vinyl}-non-3-enyl ester
• CAS No.: 120623-98-5
• Molecular Formula: C₃₂H₄₂O₇
• Molecular Weight: 538.681
• Mol file: 120623-98-5.mol

Synonyms:

Chemical Property of Benzoic acid (Z)-(R)-1-{(E)-2-[(2R,3S)-3-(3,4-dimethoxy-benzyloxy)-5-methoxy-tetrahydro-furan-2-yl]-vinyl}-non-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (Z)-(R)-1-{(E)-2-[(2R,3S)-3-(3,4-dimethoxy-benzyloxy)-5-methoxy-tetrahydro-furan-2-yl]-vinyl}-non-3-enyl ester

There total 16 articles about Benzoic acid (Z)-(R)-1-{(E)-2-[(2R,3S)-3-(3,4-dimethoxy-benzyloxy)-5-methoxy-tetrahydro-furan-2-yl]-vinyl}-non-3-enyl ester 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:

benzoyl chloride (98-88-4) + (1E,5Z)-(S)-1-[(2R,3S)-3-(3,4-Dimethoxy-benzyloxy)-5-methoxy-tetrahydro-furan-2-yl]-undeca-1,5-dien-3-ol (120623-97-4) → Benzoic acid (Z)-(S)-1-{(E)-2-[(2R,3S)-3-(3,4-dimethoxy-benzyloxy)-5-methoxy-tetrahydro-furan-2-yl]-vinyl}-non-3-enyl ester (120623-98-5)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 12h;

DOI:10.1016/S0040-4039(00)80796-0

Reference yield:

(1E,5Z)-(S)-1-[(2R,3S)-3-(3,4-Dimethoxy-benzyloxy)-5-methoxy-tetrahydro-furan-2-yl]-undeca-1,5-dien-3-ol (120623-97-4) + benzoic acid (65-85-0,8013-63-6) → Benzoic acid (Z)-(R)-1-{(E)-2-[(2R,3S)-3-(3,4-dimethoxy-benzyloxy)-5-methoxy-tetrahydro-furan-2-yl]-vinyl}-non-3-enyl ester (120623-98-5)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/S0040-4039(00)80796-0

Reference yield:

((Z)-(S)-2-Hydroxy-dec-4-enyl)-triphenyl-phosphonium; iodide (66348-37-6) → Benzoic acid (Z)-(S)-1-{(E)-2-[(2R,3S)-3-(3,4-dimethoxy-benzyloxy)-5-methoxy-tetrahydro-furan-2-yl]-vinyl}-non-3-enyl ester (120623-98-5)

Guidance literature:

Multi-step reaction with 3 steps

1: methanol / Amberlyst A-26(Cl) anion exchange column

2: 1.) sec-BuLi / 1.) THF, -30 deg C, 30 min., 2.) THF, -78 deg C to 0 deg C, 3.5 h, 0 deg C, 10 h

3: C₅H₅N / CH₂Cl₂ / 12 h / 0 °C

With pyridine; sec.-butyllithium; In methanol; dichloromethane;

DOI:10.1016/S0040-4039(00)80796-0

upstream raw materials:

benzoyl chloride

(1E,5Z)-(S)-1-[(2R,3S)-3-(3,4-Dimethoxy-benzyloxy)-5-methoxy-tetrahydro-furan-2-yl]-undeca-1,5-dien-3-ol

((Z)-(S)-2-Hydroxy-dec-4-enyl)-triphenyl-phosphonium; iodide

[(2R,3S)-3-(3,4-Dimethoxy-benzyloxy)-5-methoxy-tetrahydro-furan-2-yl]-methanol

Downstream raw materials:

Benzoic acid (2E,7Z)-(1R,4R,5S)-5-(3,4-dimethoxy-benzyloxy)-4-hydroxy-11-methoxycarbonyl-1-((Z)-oct-2-enyl)-undeca-2,7-dienyl ester

Benzoic acid (2E,7Z)-(1S,4R,5S)-5-(3,4-dimethoxy-benzyloxy)-4-hydroxy-11-methoxycarbonyl-1-((Z)-oct-2-enyl)-undeca-2,7-dienyl ester