Furan, tetrahydro-2-methyl-5-[(1R,2R)-1-methyl-2-(phenylmethoxy)-4-penten-1- yl]-, (2R,5S)-

Base Information

• Chemical Name: Furan, tetrahydro-2-methyl-5-[(1R,2R)-1-methyl-2-(phenylmethoxy)-4-penten-1- yl]-, (2R,5S)-
• CAS No.: 919608-34-7
• Molecular Formula: C18H26O2
• Molecular Weight: 274.403
• Mol file: 919608-34-7.mol

Synonyms:

Chemical Property of Furan, tetrahydro-2-methyl-5-[(1R,2R)-1-methyl-2-(phenylmethoxy)-4-penten-1- yl]-, (2R,5S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Furan, tetrahydro-2-methyl-5-[(1R,2R)-1-methyl-2-(phenylmethoxy)-4-penten-1- yl]-, (2R,5S)-

There total 12 articles about Furan, tetrahydro-2-methyl-5-[(1R,2R)-1-methyl-2-(phenylmethoxy)-4-penten-1- yl]-, (2R,5S)- 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: 90.0%

2-(5-methyl-tetrahydro-furan-2-yl)-hex-5-en-3-ol (919608-32-5) + benzyl bromide (100-39-0) → 2-(2-benzyloxy-1-methyl-pent-4-enyl)-5-methyl-tetrahydro-furan (919608-34-7)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1002/anie.200602860

Reference yield:

methanesulfonic acid 5-(1-methyl-2-oxo-ethyl)-tetrahydro-furan-2-ylmethyl ester (919608-15-4) → 2-(2-benzyloxy-1-methyl-pent-4-enyl)-5-methyl-tetrahydro-furan (919608-34-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: TiCl₄ / CH₂Cl₂ / 0.25 h / -78 °C

1.2: 95 percent / CH₂Cl₂ / 0.5 h / -78 °C

2.1: 66 percent / lithium aluminum hydride / diethyl ether / 0 - 20 °C

3.1: 90 percent / sodium hexamethyldisilazide / tetrahydrofuran; dimethylformamide / 0 - 20 °C

With lithium aluminium tetrahydride; sodium hexamethyldisilazane; titanium tetrachloride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2007.07.005

Reference yield:

{5-[2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-tetrahydro-furan-2-yl}-methanol (919608-13-2) → 2-(2-benzyloxy-1-methyl-pent-4-enyl)-5-methyl-tetrahydro-furan (919608-34-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 98 percent / TEA / CH₂Cl₂ / 0 - 20 °C

2.1: 95 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

3.1: 82 percent / PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 20 °C

4.1: TiCl₄ / CH₂Cl₂ / 0.25 h / -78 °C

4.2: 95 percent / CH₂Cl₂ / 0.5 h / -78 °C

5.1: 66 percent / lithium aluminum hydride / diethyl ether / 0 - 20 °C

6.1: 90 percent / sodium hexamethyldisilazide / tetrahydrofuran; dimethylformamide / 0 - 20 °C

With lithium aluminium tetrahydride; 4 A molecular sieve; TEA; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; titanium tetrachloride; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2007.07.005

upstream raw materials:

2-(5-methyl-tetrahydro-furan-2-yl)-hex-5-en-3-ol

benzyl bromide

methanesulfonic acid 5-(1-methyl-2-oxo-ethyl)-tetrahydro-furan-2-ylmethyl ester

5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-pentane-1,3-diol

Downstream raw materials:

5-benzyloxy-3-hydroxy-6-(5-methyl-tetrahydro-furan-2-yl)-heptanal

6-benzyloxy-7-(5-methyl-tetrahydro-furan-2-yl)-oct-1-en-4-ol

5-benzyloxy-6-(5-methyl-tetrahydro-furan-2-yl)-heptane-1,3-diol

C₂₃H₃₅IO₃