(-)-(2S,3R,4R)-2-(Benzyloxy)-4-<3,4-(methylenedioxy)benzoyl>-3-<3,4-(methylenedioxy)benzyl>tetrahydrofuran

Base Information

• Chemical Name: (-)-(2S,3R,4R)-2-(Benzyloxy)-4-<3,4-(methylenedioxy)benzoyl>-3-<3,4-(methylenedioxy)benzyl>tetrahydrofuran
• CAS No.: 120040-66-6
• Molecular Formula: C₂₇H₂₄O₇
• Molecular Weight: 460.483
• Mol file: 120040-66-6.mol

Synonyms:(-)-(2S,3R,4R)-2-(Benzyloxy)-4-<3,4-(methylenedioxy)benzoyl>-3-<3,4-(methylenedioxy)benzyl>tetrahydrofuran

Chemical Property of (-)-(2S,3R,4R)-2-(Benzyloxy)-4-<3,4-(methylenedioxy)benzoyl>-3-<3,4-(methylenedioxy)benzyl>tetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(2S,3R,4R)-2-(Benzyloxy)-4-<3,4-(methylenedioxy)benzoyl>-3-<3,4-(methylenedioxy)benzyl>tetrahydrofuran

There total 9 articles about (-)-(2S,3R,4R)-2-(Benzyloxy)-4-<3,4-(methylenedioxy)benzoyl>-3-<3,4-(methylenedioxy)benzyl>tetrahydrofuran 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: 49.0%

(+)-(2S,3S,4R)-2-(Benzyloxy)-4-<3,4-(methylenedioxy)benzoyl>-3-<<3,4-(methylenedioxy)phenyl>bis(phenylthio)methyl>tetrahydrofuran (120040-64-4) → (-)-(2S,3R,4R)-2-(Benzyloxy)-4-<3,4-(methylenedioxy)benzoyl>-3-<3,4-(methylenedioxy)benzyl>tetrahydrofuran (120040-66-6)

Guidance literature:

With nickel; In ethanol; ethyl acetate;

DOI:10.1021/jo00301a026

Reference yield:

(+)-(2R)-benzyloxy-2,5-dihydrofuran-4-carboxaldehyde (104322-41-0) → (-)-(2S,3R,4R)-2-(Benzyloxy)-4-<3,4-(methylenedioxy)benzoyl>-3-<3,4-(methylenedioxy)benzyl>tetrahydrofuran (120040-66-6)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran / 0 °C

2: CrO₃ / pyridine; CH₂Cl₂ / 0.25 h / 22 °C

3: 78 percent / n-buthyllithium / tetrahydrofuran / 0.33 h / -78 °C

4: Raney-nickel / 1,2-dimethoxy-ethane / 0 °C

With chromium(VI) oxide; n-butyllithium; nickel; In tetrahydrofuran; pyridine; 1,2-dimethoxyethane; dichloromethane;

DOI:10.1016/0040-4039(88)85304-8

Reference yield:

Benzo[1,3]dioxol-5-yl-((R)-5-benzyloxy-2,5-dihydro-furan-3-yl)-methanol (120040-58-6) → (-)-(2S,3R,4R)-2-(Benzyloxy)-4-<3,4-(methylenedioxy)benzoyl>-3-<3,4-(methylenedioxy)benzyl>tetrahydrofuran (120040-66-6)

Guidance literature:

Multi-step reaction with 3 steps

1: CrO₃ / pyridine; CH₂Cl₂ / 0.25 h / 22 °C

2: 78 percent / n-buthyllithium / tetrahydrofuran / 0.33 h / -78 °C

3: Raney-nickel / 1,2-dimethoxy-ethane / 0 °C

With chromium(VI) oxide; n-butyllithium; nickel; In tetrahydrofuran; pyridine; 1,2-dimethoxyethane; dichloromethane;

DOI:10.1016/0040-4039(88)85304-8

upstream raw materials:

(+)-(2S,3S,4R)-2-(Benzyloxy)-4-<3,4-(methylenedioxy)benzoyl>-3-<<3,4-(methylenedioxy)phenyl>bis(phenylthio)methyl>tetrahydrofuran

(-)-(2R)-2-(Benzyloxy)-2,5-dihydro-4-<3,4-(methylenedioxy)benzoyl>furan

benzo[d][1,3]dioxol-5-ylmethyl methyl ether

piperonal

Downstream raw materials:

(2S,3R,4R)-5-((4-(benzo[d][1,3]dioxol-5-ylmethyl)-2-isopropoxytetrahydrofuran-3-yl)methyl)benzo[d][1,3]dioxole

(2R,3R,4R)-5-((4-(benzo[d][1,3]dioxol-5-ylmethyl)-2-isopropoxytetrahydrofuran-3-yl)methyl)benzo[d][1,3]dioxole

(8R,8'R-)8,8'-bis-(3'4'-methylenedioxybenzyl)-tetrahydrofuran (-)-dehydroxycubebin