3,4-bis(benzyloxy)tetrahydro-5-methoxy-2-methyl-2-vinylfuran

Base Information

• Chemical Name: 3,4-bis(benzyloxy)tetrahydro-5-methoxy-2-methyl-2-vinylfuran
• CAS No.: 864712-68-5
• Molecular Formula: C₂₂H₂₆O₄
• Molecular Weight: 354.446
• Mol file: 864712-68-5.mol

Synonyms:3,4-bis(benzyloxy)tetrahydro-5-methoxy-2-methyl-2-vinylfuran

Chemical Property of 3,4-bis(benzyloxy)tetrahydro-5-methoxy-2-methyl-2-vinylfuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4-bis(benzyloxy)tetrahydro-5-methoxy-2-methyl-2-vinylfuran

There total 2 articles about 3,4-bis(benzyloxy)tetrahydro-5-methoxy-2-methyl-2-vinylfuran 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:

methyl 2,3-di-O-benzyl-6-iodo-4-C-methyl-α-D-glucopyranoside (887768-96-9) → 3,4-bis(benzyloxy)tetrahydro-5-methoxy-2-methyl-2-vinylfuran (864712-68-5)

Guidance literature:

methyl 2,3-di-O-benzyl-6-iodo-4-C-methyl-α-D-glucopyranoside; With zinc; In ethanol; for 15h; Heating;

With Amberlyst 15E; In methanol; for 17h; Heating;

DOI:10.1246/bcsj.79.468

Reference yield:

4,5-bis-benzyloxy-2-(4-methanesulfonyl-phenoxymethyl)-6-methoxy-3-methyl-tetrahydro-pyran-3-ol → 3,4-bis(benzyloxy)tetrahydro-5-methoxy-2-methyl-2-vinylfuran (864712-68-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 92 percent / NaI / dimethylformamide / 14 h / 95 °C

2.1: Zn / ethanol / 15 h / Heating

2.2: 5.9 g / amberlyst 15E / methanol / 17 h / Heating

With sodium iodide; zinc; In ethanol; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.79.468

Reference yield: 97.0%

3,4-bis(benzyloxy)tetrahydro-5-methoxy-2-methyl-2-vinylfuran (864712-68-5) → 2-((2R,3R,4R)-3,4-Bis-benzyloxy-5-methoxy-2-methyl-tetrahydro-furan-2-yl)-ethanol (887769-08-6)

Guidance literature:

With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1246/bcsj.79.468

upstream raw materials:

methyl 2,3-di-O-benzyl-6-iodo-4-C-methyl-α-D-glucopyranoside

Downstream raw materials:

2-((2R,3R,4R)-3,4-Bis-benzyloxy-5-methoxy-2-methyl-tetrahydro-furan-2-yl)-ethanol

((2R,3R,4R)-3,4-Bis-benzyloxy-5-methoxy-2-methyl-tetrahydro-furan-2-yl)-acetaldehyde

[(E)-6-((2R,3R,4R)-3,4-Bis-benzyloxy-5-methoxy-2-methyl-tetrahydro-furan-2-yl)-hex-4-enyloxy]-tert-butyl-diphenyl-silane

{6-[3,4-bis(benzyloxy)tetrahydro-5-methoxy-2-methylfuran-2-yl]hexyloxy}(t-butyl)diphenylsilane