(1R,2R,6R,8R,9R)-1,9-Bis(benzyloxy)-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.0^2.6]undec-10-ene

Base Information

• Chemical Name: (1R,2R,6R,8R,9R)-1,9-Bis(benzyloxy)-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.0^2.6]undec-10-ene
• CAS No.: 352422-83-4
• Molecular Formula: C₂₄H₂₆O₅
• Molecular Weight: 394.467

Synonyms:(1R,2R,6R,8R,9R)-1,9-Bis(benzyloxy)-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.0^2.6]undec-10-ene

Chemical Property of (1R,2R,6R,8R,9R)-1,9-Bis(benzyloxy)-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.0^2.6]undec-10-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,6R,8R,9R)-1,9-Bis(benzyloxy)-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.0^2.6]undec-10-ene

There total 12 articles about (1R,2R,6R,8R,9R)-1,9-Bis(benzyloxy)-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.0^2.6]undec-10-ene 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: 97.0%

benzyl bromide (100-39-0) + (1R,2R,6R,8R,9R)-1-Benzyloxy-9-hydroxy-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.02.6]undec-10-ene (352422-88-9) → (1R,2R,6R,8R,9R)-1,9-Bis(benzyloxy)-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.02.6]undec-10-ene (352422-83-4)

Guidance literature:

(1R,2R,6R,8R,9R)-1-Benzyloxy-9-hydroxy-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.0^2.6]undec-10-ene; With sodium hydride; In N,N-dimethyl-formamide; at 50 ℃; for 1h;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃; for 16h; Further stages.;

DOI:10.1039/b101364p

Reference yield: 80.0%

benzyl bromide (100-39-0) + (1R,2R,6R,8R,9R)-1,9-Dihydroxy-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.02.6]undec-10-ene (352422-81-2) → (1R,2R,6R,8R,9R)-1,9-Bis(benzyloxy)-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.02.6]undec-10-ene (352422-83-4)

Guidance literature:

(1R,2R,6R,8R,9R)-1,9-Dihydroxy-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.0^2.6]undec-10-ene; With sodium hydride; In N,N-dimethyl-formamide; at 50 ℃; for 1h;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃; for 16h; Further stages.;

DOI:10.1039/b101364p

Reference yield:

(3aR,5R,6R,6aR)-6-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro-[2,3-d][1,3]dioxole (96212-44-1) → (1R,2R,6R,8R,9R)-1,9-Bis(benzyloxy)-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.02.6]undec-10-ene (352422-83-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: periodic acid / ethyl acetate / 1 h / 20 °C

2.1: tetrahydrofuran / 48 h / 20 °C

3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene](benzylidene)Ru(II) dichloride / dichloromethane / 1 h / 40 °C

4.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 50 °C

4.2: 27 / 16 h / 20 °C

With sodium hydride; periodic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene](benzylidene)Ru(II) dichloride; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 2.1: Grignard addition;

DOI:10.1039/b101364p

upstream raw materials:

benzyl bromide

(1R,2R,6R,8R,9R)-1,9-Dihydroxy-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.0^2.6]undec-10-ene

(1R,2R,6R,8R,9R)-1-Benzyloxy-9-hydroxy-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.0^2.6]undec-10-ene

(3aR,5R,6R,6aR)-6-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro-[2,3-d][1,3]dioxole

Downstream raw materials:

(3R/S,1R,4R,5R,8R)-3,4-Diacetoxy-5,8-bis(benzyloxy)-2-oxabicyclo[3.3.0]oct-6-ene

(1R,3R,5R,8R)-5,8-Bis(benzyloxy)-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]octane

(1R,3R,4R,5R,8R)-5,8-Bis(benzyloxy)-4-hydroxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene

(1R,3R,4R,5R,8R)-4-Acetoxy-5,8-bis(benzyloxy)-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene

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