(3S,5S,6R)-6-((1S,3R)-4-Benzyloxy-1-methoxy-3-methyl-butyl)-5-methoxy-3-{(E)-(R)-4-[(S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-2-methyl-hepta-2,6-dienyl}-tetrahydro-pyran-2-one

Base Information

• Chemical Name: (3S,5S,6R)-6-((1S,3R)-4-Benzyloxy-1-methoxy-3-methyl-butyl)-5-methoxy-3-{(E)-(R)-4-[(S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-2-methyl-hepta-2,6-dienyl}-tetrahydro-pyran-2-one
• CAS No.: 128461-62-1
• Molecular Formula: C₃₈H₅₂O₈
• Molecular Weight: 636.826
• Mol file: 128461-62-1.mol

Synonyms:(3S,5S,6R)-6-((1S,3R)-4-Benzyloxy-1-methoxy-3-methyl-butyl)-5-methoxy-3-{(E)-(R)-4-[(S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-2-methyl-hepta-2,6-dienyl}-tetrahydro-pyran-2-one

Chemical Property of (3S,5S,6R)-6-((1S,3R)-4-Benzyloxy-1-methoxy-3-methyl-butyl)-5-methoxy-3-{(E)-(R)-4-[(S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-2-methyl-hepta-2,6-dienyl}-tetrahydro-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5S,6R)-6-((1S,3R)-4-Benzyloxy-1-methoxy-3-methyl-butyl)-5-methoxy-3-{(E)-(R)-4-[(S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-2-methyl-hepta-2,6-dienyl}-tetrahydro-pyran-2-one

There total 21 articles about (3S,5S,6R)-6-((1S,3R)-4-Benzyloxy-1-methoxy-3-methyl-butyl)-5-methoxy-3-{(E)-(R)-4-[(S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-2-methyl-hepta-2,6-dienyl}-tetrahydro-pyran-2-one 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: 80.0%

(2R,4S)-4-((E)-(R)-1-Allyl-4-iodo-3-methyl-but-2-enyl)-2-(4-methoxy-phenyl)-[1,3]dioxane (128461-51-8) + (5S,6R)-6-((1S,3R)-4-Benzyloxy-1-methoxy-3-methyl-butyl)-5-methoxy-tetrahydro-pyran-2-one (128461-50-7) → (3S,5S,6R)-6-((1S,3R)-4-Benzyloxy-1-methoxy-3-methyl-butyl)-5-methoxy-3-{(E)-(R)-4-[(S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-2-methyl-hepta-2,6-dienyl}-tetrahydro-pyran-2-one (128461-62-1)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(00)70631-9

Reference yield:

benzyl bromide (100-39-0) → (3S,5S,6R)-6-((1S,3R)-4-Benzyloxy-1-methoxy-3-methyl-butyl)-5-methoxy-3-{(E)-(R)-4-[(S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-2-methyl-hepta-2,6-dienyl}-tetrahydro-pyran-2-one (128461-62-1)

Guidance literature:

Multi-step reaction with 12 steps

2: AcOH / tetrahydrofuran; H₂O / 50 °C

3: imidazole / dimethylformamide

4: 90 percent / t-BuOOH / (+)-DIPT, Ti(i-PrO)4 / CH₂Cl₂ / -20 °C

5: NaH / tetrahydrofuran / 0 °C

6: n-Bu₄NF / tetrahydrofuran

7: Dess-Martin periodinane reagent

8: tetrahydrofuran

9: H₂ / Pd/C / ethyl acetate

10: 1.) NaOH / 2.) CSA / 1.) EtOH, reflux; 2.) CH₂Cl₂

11: boron trifluoride etherate / 0 °C

12: 80 percent / sodium hexamethyldisilazide / tetrahydrofuran / -78 °C

With 1H-imidazole; tert.-butylhydroperoxide; sodium hydroxide; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; sodium hydride; Dess-Martin periodane; acetic acid; titanium(IV) isopropylate; palladium on activated charcoal; L-(+)-diisopropyl tartrate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)70631-9

Reference yield:

Propionic acid (R)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-allyl ester → (3S,5S,6R)-6-((1S,3R)-4-Benzyloxy-1-methoxy-3-methyl-butyl)-5-methoxy-3-{(E)-(R)-4-[(S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-2-methyl-hepta-2,6-dienyl}-tetrahydro-pyran-2-one (128461-62-1)

Guidance literature:

Multi-step reaction with 12 steps

2: AcOH / tetrahydrofuran; H₂O / 50 °C

3: imidazole / dimethylformamide

4: 90 percent / t-BuOOH / (+)-DIPT, Ti(i-PrO)4 / CH₂Cl₂ / -20 °C

5: NaH / tetrahydrofuran / 0 °C

6: n-Bu₄NF / tetrahydrofuran

7: Dess-Martin periodinane reagent

8: tetrahydrofuran

9: H₂ / Pd/C / ethyl acetate

10: 1.) NaOH / 2.) CSA / 1.) EtOH, reflux; 2.) CH₂Cl₂

11: boron trifluoride etherate / 0 °C

12: 80 percent / sodium hexamethyldisilazide / tetrahydrofuran / -78 °C

With 1H-imidazole; tert.-butylhydroperoxide; sodium hydroxide; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; sodium hydride; Dess-Martin periodane; acetic acid; titanium(IV) isopropylate; palladium on activated charcoal; L-(+)-diisopropyl tartrate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)70631-9

upstream raw materials:

(2R,4S)-4-((E)-(R)-1-Allyl-4-iodo-3-methyl-but-2-enyl)-2-(4-methoxy-phenyl)-[1,3]dioxane

(5S,6R)-6-((1S,3R)-4-Benzyloxy-1-methoxy-3-methyl-butyl)-5-methoxy-tetrahydro-pyran-2-one

benzyl bromide

3-(p-methoxybenzyloxy)propanal

Downstream raw materials:

Toluene-4-sulfonic acid (E)-(2S,6R)-2-[(2S,3S,4S,6R)-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethoxy-6-methyl-heptyl]-6-[(2R,4S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-4-methyl-nona-4,8-dienyl ester

Toluene-4-sulfonic acid (E)-(2S,6R)-2-((2S,3S,4S,6R)-7-benzyloxy-3-hydroxy-2,4-dimethoxy-6-methyl-heptyl)-6-[(2R,4S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-4-methyl-nona-4,8-dienyl ester

{(E)-(1R,2S,4S,8R)-1-((1S,3R)-4-Benzyloxy-1-methoxy-3-methyl-butyl)-2-methoxy-8-[(2R,4R)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-4,6-dimethyl-undeca-6,10-dienyloxy}-tert-butyl-dimethyl-silane

(E)-(2R,4S,5S,6S,8S,12R)-1-Benzyloxy-8-hydroxymethyl-4,6-dimethoxy-12-[(2R,4S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-2,10-dimethyl-pentadeca-10,14-dien-5-ol