5-[(E)-3-((2R,6S)-6-Benzyloxymethyl-tetrahydro-pyran-2-yl)-propenyl]-2,2-dimethyl-benzo[1,3]dioxin-4-one

Base Information

• Chemical Name: 5-[(E)-3-((2R,6S)-6-Benzyloxymethyl-tetrahydro-pyran-2-yl)-propenyl]-2,2-dimethyl-benzo[1,3]dioxin-4-one
• CAS No.: 863660-04-2
• Molecular Formula: C₂₆H₃₀O₅
• Molecular Weight: 422.521
• Mol file: 863660-04-2.mol

Synonyms:5-[(E)-3-((2R,6S)-6-Benzyloxymethyl-tetrahydro-pyran-2-yl)-propenyl]-2,2-dimethyl-benzo[1,3]dioxin-4-one

Chemical Property of 5-[(E)-3-((2R,6S)-6-Benzyloxymethyl-tetrahydro-pyran-2-yl)-propenyl]-2,2-dimethyl-benzo[1,3]dioxin-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-[(E)-3-((2R,6S)-6-Benzyloxymethyl-tetrahydro-pyran-2-yl)-propenyl]-2,2-dimethyl-benzo[1,3]dioxin-4-one

There total 7 articles about 5-[(E)-3-((2R,6S)-6-Benzyloxymethyl-tetrahydro-pyran-2-yl)-propenyl]-2,2-dimethyl-benzo[1,3]dioxin-4-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: 98.0%

[(E)-3-((2R,6S)-6-Benzyloxymethyl-tetrahydro-pyran-2-yl)-propenyl]-tributyl-stannane + 2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H-(1,3)benzodioxin-4-one (164014-40-8) → 5-[(E)-3-((2R,6S)-6-Benzyloxymethyl-tetrahydro-pyran-2-yl)-propenyl]-2,2-dimethyl-benzo[1,3]dioxin-4-one (863660-04-2)

Guidance literature:

With triphenylphosphine; lithium chloride; bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 120 ℃; for 6h;

DOI:10.1021/jo0507993

Reference yield: 87.0%

C22H33BO4 + 2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H-(1,3)benzodioxin-4-one (164014-40-8) → 5-[(E)-3-((2R,6S)-6-Benzyloxymethyl-tetrahydro-pyran-2-yl)-propenyl]-2,2-dimethyl-benzo[1,3]dioxin-4-one (863660-04-2)

Guidance literature:

With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; Inert atmosphere;

DOI:10.1021/ol8011474

Reference yield: 70.0%

(2S,6R)-2-Benzyloxymethyl-6-[(E)-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-allyl]-tetrahydro-pyran (863660-12-2) + 2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H-(1,3)benzodioxin-4-one (164014-40-8) → 5-[(E)-3-((2R,6S)-6-Benzyloxymethyl-tetrahydro-pyran-2-yl)-propenyl]-2,2-dimethyl-benzo[1,3]dioxin-4-one (863660-04-2)

Guidance literature:

(2S,6R)-2-Benzyloxymethyl-6-[(E)-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-allyl]-tetrahydro-pyran; 2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H-(1,3)benzodioxin-4-one; With potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; at 60 ℃; for 24h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran;

DOI:10.1021/jo0507993

upstream raw materials:

(2S,6R)-2-Benzyloxymethyl-6-[(E)-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-allyl]-tetrahydro-pyran

2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H-(1,3)benzodioxin-4-one

2,6-Dihydroxybenzoic acid

5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one

Downstream raw materials:

2-[6-(2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-7-{6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-5-methyl-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

2-Hydroxy-6-[3-((2S,6S)-6-vinyl-tetrahydro-pyran-2-yl)-propyl]-benzoic acid (1R,2S)-1-((S)-2-benzyloxy-3-{(2S,6R)-6-[1-methyl-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-tetrahydro-pyran-2-yl}-propyl)-2-methyl-but-3-enyl ester