5-(6,7-dihydroxy-3,7-dimethyloct-2E-enyl)-5-methoxycarbonylhex-2E-enedioic acid 1-benzyl ester 6-methyl ester

Base Information

• Chemical Name: 5-(6,7-dihydroxy-3,7-dimethyloct-2E-enyl)-5-methoxycarbonylhex-2E-enedioic acid 1-benzyl ester 6-methyl ester
• CAS No.: 852402-33-6
• Molecular Formula: C₂₆H₃₆O₈
• Molecular Weight: 476.567
• Mol file: 852402-33-6.mol

Synonyms:5-(6,7-dihydroxy-3,7-dimethyloct-2E-enyl)-5-methoxycarbonylhex-2E-enedioic acid 1-benzyl ester 6-methyl ester

Chemical Property of 5-(6,7-dihydroxy-3,7-dimethyloct-2E-enyl)-5-methoxycarbonylhex-2E-enedioic acid 1-benzyl ester 6-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(6,7-dihydroxy-3,7-dimethyloct-2E-enyl)-5-methoxycarbonylhex-2E-enedioic acid 1-benzyl ester 6-methyl ester

There total 1 articles about 5-(6,7-dihydroxy-3,7-dimethyloct-2E-enyl)-5-methoxycarbonylhex-2E-enedioic acid 1-benzyl ester 6-methyl 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: 87.0%

5-(3,7-dimethylocta-2E,6-dienyl)-5-methoxycarbonylhex-2E-enedioic acid 1-benzyl ester 6-dimethyl ester (852402-27-8) → 5-(6,7-dihydroxy-3,7-dimethyloct-2E-enyl)-5-methoxycarbonylhex-2E-enedioic acid 1-benzyl ester 6-methyl ester (852402-33-6)

Guidance literature:

With AD-mix-α; methanesulfonamide; In water; tert-butyl alcohol; at 0 ℃; for 14h;

DOI:10.1021/ja042595u

Reference yield: 89.0%

5-(6,7-dihydroxy-3,7-dimethyloct-2E-enyl)-5-methoxycarbonylhex-2E-enedioic acid 1-benzyl ester 6-methyl ester (852402-33-6) → 5-methoxycarbonyl-5-(3-methyl-6-oxohex-2E-enyl)hex-2E-enedioic acid 1-benzyl ester 6-methyl ester (852402-36-9)

Guidance literature:

With sodium periodate; In tetrahydrofuran; for 17h;

DOI:10.1021/ja042595u

Reference yield:

5-(6,7-dihydroxy-3,7-dimethyloct-2E-enyl)-5-methoxycarbonylhex-2E-enedioic acid 1-benzyl ester 6-methyl ester (852402-33-6) → 5-(7-iodo-3-methylhepta-2E,6Z-dienyl)-5-methoxycarbonylhex-2E-enedioic acid 1-benzyl ester 6-methyl ester (852402-40-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 89 percent / aq. NaIO₄ / tetrahydrofuran / 17 h

2.1: NaHMDS / tetrahydrofuran / 0.5 h / 20 °C

2.2: tetrahydrofuran / -78 - 20 °C

With sodium periodate; sodium hexamethyldisilazane; In tetrahydrofuran; 2.2: Wittig olefination;

DOI:10.1021/ja042595u

upstream raw materials:

5-(3,7-dimethylocta-2E,6-dienyl)-5-methoxycarbonylhex-2E-enedioic acid 1-benzyl ester 6-dimethyl ester

Downstream raw materials:

5-methoxycarbonyl-5-(3-methyl-6-oxohex-2E-enyl)hex-2E-enedioic acid 1-benzyl ester 6-methyl ester

5-(7-iodo-3-methylhepta-2E,6Z-dienyl)-5-methoxycarbonylhex-2E-enedioic acid 1-benzyl ester 6-methyl ester