(3E,5E)-7-[2-(4-Benzyloxy-3-benzyloxymethyl-1-hydroxy-butyl)-tetrahydro-furan-2-yloxy]-4-methyl-hepta-3,5-dien-1-ol

Base Information

• Chemical Name: (3E,5E)-7-[2-(4-Benzyloxy-3-benzyloxymethyl-1-hydroxy-butyl)-tetrahydro-furan-2-yloxy]-4-methyl-hepta-3,5-dien-1-ol
• CAS No.: 717919-09-0
• Molecular Formula: C₃₁H₄₂O₆
• Molecular Weight: 510.671

Synonyms:(3E,5E)-7-[2-(4-Benzyloxy-3-benzyloxymethyl-1-hydroxy-butyl)-tetrahydro-furan-2-yloxy]-4-methyl-hepta-3,5-dien-1-ol

Chemical Property of (3E,5E)-7-[2-(4-Benzyloxy-3-benzyloxymethyl-1-hydroxy-butyl)-tetrahydro-furan-2-yloxy]-4-methyl-hepta-3,5-dien-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3E,5E)-7-[2-(4-Benzyloxy-3-benzyloxymethyl-1-hydroxy-butyl)-tetrahydro-furan-2-yloxy]-4-methyl-hepta-3,5-dien-1-ol

There total 13 articles about (3E,5E)-7-[2-(4-Benzyloxy-3-benzyloxymethyl-1-hydroxy-butyl)-tetrahydro-furan-2-yloxy]-4-methyl-hepta-3,5-dien-1-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: 85.0%

2-[4-benzyloxy-3-benzyloxymethyl-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-2-[7-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hepta-2,4-dienyloxy]-tetrahydro-furan (717918-95-1) → (3E,5E)-7-[2-(4-Benzyloxy-3-benzyloxymethyl-1-hydroxy-butyl)-tetrahydro-furan-2-yloxy]-4-methyl-hepta-3,5-dien-1-ol (717919-09-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/ol0495624

Reference yield:

(2-propenyl)propanedioic acid diethyl ester (2049-80-1) → (3E,5E)-7-[2-(4-Benzyloxy-3-benzyloxymethyl-1-hydroxy-butyl)-tetrahydro-furan-2-yloxy]-4-methyl-hepta-3,5-dien-1-ol (717919-09-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 84 percent / LAH / diethyl ether / 0 - 20 °C

2.1: 100 percent / NaH / tetrahydrofuran; dimethylformamide / 0 - 20 °C

3.1: 96 percent / N-methylmorpholine N-oxide / K₂OsO₄*2H₂O / acetone; H₂O / 12 h / 20 °C

4.1: 90 percent / NaIO₄ / tetrahydrofuran; H₂O / 0 - 20 °C

5.1: t-BuLi / tetrahydrofuran; pentane / -78 - 0 °C

5.2: tetrahydrofuran; pentane / 1 h / -78 °C

6.1: 17.0 g / imidazole / CH₂Cl₂ / 0 - 20 °C

7.1: 79 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 0 - 20 °C

8.1: 85 percent / TBAF / tetrahydrofuran / 0 - 20 °C

With 1H-imidazole; sodium periodate; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydride; 4-methylmorpholine N-oxide; potassium osmate(VI); In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; pentane;

DOI:10.1021/ol0495624

Reference yield:

2-allyl-1,3-propanediol (42201-43-4) → (3E,5E)-7-[2-(4-Benzyloxy-3-benzyloxymethyl-1-hydroxy-butyl)-tetrahydro-furan-2-yloxy]-4-methyl-hepta-3,5-dien-1-ol (717919-09-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 100 percent / NaH / tetrahydrofuran; dimethylformamide / 0 - 20 °C

2.1: 96 percent / N-methylmorpholine N-oxide / K₂OsO₄*2H₂O / acetone; H₂O / 12 h / 20 °C

3.1: 90 percent / NaIO₄ / tetrahydrofuran; H₂O / 0 - 20 °C

4.1: t-BuLi / tetrahydrofuran; pentane / -78 - 0 °C

4.2: tetrahydrofuran; pentane / 1 h / -78 °C

5.1: 17.0 g / imidazole / CH₂Cl₂ / 0 - 20 °C

6.1: 79 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 0 - 20 °C

7.1: 85 percent / TBAF / tetrahydrofuran / 0 - 20 °C

With 1H-imidazole; sodium periodate; tetrabutyl ammonium fluoride; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydride; 4-methylmorpholine N-oxide; potassium osmate(VI); In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; pentane;

DOI:10.1021/ol0495624

upstream raw materials:

2-[4-benzyloxy-3-benzyloxymethyl-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-2-[7-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hepta-2,4-dienyloxy]-tetrahydro-furan

(2-propenyl)propanedioic acid diethyl ester

2-allyl-1,3-propanediol

4-benzyloxy-3-benzyloxymethylbutyraldehyde

Downstream raw materials:

4-Benzyloxy-3-benzyloxymethyl-1-{2-[(2E,4E)-7-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hepta-2,4-dienyloxy]-tetrahydro-furan-2-yl}-butan-1-ol

4-Benzyloxy-3-benzyloxymethyl-1-{2-[(2E,4E)-7-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hepta-2,4-dienyloxy]-tetrahydro-furan-2-yl}-butan-1-one

4-Benzyloxy-3-benzyloxymethyl-1-{2-[(2E,4E)-7-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hepta-2,4-dienyloxy]-tetrahydro-furan-2-yl}-2-methylene-butan-1-one

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