(2R,6R)-2-(3-Benzyloxy-propyl)-6-(3-methyl-but-2-enyl)-3,6-dihydro-2H-pyran

Base Information

• Chemical Name: (2R,6R)-2-(3-Benzyloxy-propyl)-6-(3-methyl-but-2-enyl)-3,6-dihydro-2H-pyran
• CAS No.: 224947-56-2
• Molecular Formula: C₂₀H₂₈O₂
• Molecular Weight: 300.441
• Mol file: 224947-56-2.mol

Synonyms:(2R,6R)-2-(3-Benzyloxy-propyl)-6-(3-methyl-but-2-enyl)-3,6-dihydro-2H-pyran

Chemical Property of (2R,6R)-2-(3-Benzyloxy-propyl)-6-(3-methyl-but-2-enyl)-3,6-dihydro-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,6R)-2-(3-Benzyloxy-propyl)-6-(3-methyl-but-2-enyl)-3,6-dihydro-2H-pyran

There total 1 articles about (2R,6R)-2-(3-Benzyloxy-propyl)-6-(3-methyl-but-2-enyl)-3,6-dihydro-2H-pyran 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: 40.0%

isopropyltriphenylphosphonium bromide (1530-33-2) + [(2R,6R)-6-(3-Benzyloxy-propyl)-5,6-dihydro-2H-pyran-2-yl]-acetaldehyde (194423-23-9) → (2R,6R)-2-(3-Benzyloxy-propyl)-6-(3-methyl-but-2-enyl)-3,6-dihydro-2H-pyran (224947-56-2)

Guidance literature:

With n-butyllithium; In diethyl ether; at 0 ℃;

DOI:10.1016/S0040-4039(99)00214-2

Reference yield:

(2R,6R)-2-(3-Benzyloxy-propyl)-6-(3-methyl-but-2-enyl)-3,6-dihydro-2H-pyran (224947-56-2) → (R)-1-[(2R,6R)-6-(3-Benzyloxy-propyl)-5,6-dihydro-2H-pyran-2-yl]-3-methyl-butane-2,3-diol + (S)-1-[(2R,6R)-6-(3-Benzyloxy-propyl)-5,6-dihydro-2H-pyran-2-yl]-3-methyl-butane-2,3-diol

Guidance literature:

With methanesulfonamide; AD-mix-β; In water; tert-butyl alcohol; at 0 - 20 ℃; Yield given; Yields of byproduct given;

DOI:10.1016/S0040-4039(99)00214-2

Reference yield:

(2R,6R)-2-(3-Benzyloxy-propyl)-6-(3-methyl-but-2-enyl)-3,6-dihydro-2H-pyran (224947-56-2) → (2R,3S,4S,6R)-6-(3-Benzyloxy-propyl)-2-((S)-5,5-dimethyl-2-oxo-2λ4-[1,3,2]dioxathiolan-4-ylmethyl)-tetrahydro-pyran-3,4-diol

Guidance literature:

Multi-step reaction with 3 steps

1: AD-mix-α, MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 0 - 20 °C

2: 95 percent / SOCl₂, imidazole / tetrahydrofuran / -20 - 20 °C

3: RuCl₃*3H₃O, NaIO₄ / ethyl acetate; acetonitrile; H₂O / 0.17 h / 0 - 20 °C

With 1H-imidazole; ruthenium trichloride; sodium periodate; AD-mix-α; thionyl chloride; methanesulfonamide; In tetrahydrofuran; water; ethyl acetate; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0040-4039(99)00214-2

upstream raw materials:

isopropyltriphenylphosphonium bromide

[(2R,6R)-6-(3-Benzyloxy-propyl)-5,6-dihydro-2H-pyran-2-yl]-acetaldehyde

Downstream raw materials:

(2R,6R)-2-(3-Benzyloxy-propyl)-6-((R)-5,5-dimethyl-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-ylmethyl)-3,6-dihydro-2H-pyran

(2R,6R)-2-(3-Benzyloxy-propyl)-6-((S)-5,5-dimethyl-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-ylmethyl)-3,6-dihydro-2H-pyran