(1R,6R,7S)-6-benzyl-7-carbethoxy-2-oxabicyclo[4.1.0]heptane

Base Information

• Chemical Name: (1R,6R,7S)-6-benzyl-7-carbethoxy-2-oxabicyclo[4.1.0]heptane
• CAS No.: 213137-46-3
• Molecular Formula: C₁₆H₂₀O₃
• Molecular Weight: 260.333
• Mol file: 213137-46-3.mol

Synonyms:(1R,6R,7S)-6-benzyl-7-carbethoxy-2-oxabicyclo[4.1.0]heptane

Chemical Property of (1R,6R,7S)-6-benzyl-7-carbethoxy-2-oxabicyclo[4.1.0]heptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,6R,7S)-6-benzyl-7-carbethoxy-2-oxabicyclo[4.1.0]heptane

There total 5 articles about (1R,6R,7S)-6-benzyl-7-carbethoxy-2-oxabicyclo[4.1.0]heptane 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: 67.0%

diazoacetic acid ethyl ester (623-73-4) + 5-benzyl-3,4-dihydro-2H-pyran (87143-16-6) → (1R,6R,7S)-6-benzyl-7-carbethoxy-2-oxabicyclo[4.1.0]heptane (213137-46-3) + endo-6-benzyl-7-carbethoxy-2-oxabicyclo[4.1.0]heptane

Guidance literature:

With 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline]; copper(I) trifluoromethanesulfonate benzene; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jo9807417

Reference yield:

3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9) → (1R,6R,7S)-6-benzyl-7-carbethoxy-2-oxabicyclo[4.1.0]heptane (213137-46-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: DIPA; n-BuLi / tetrahydrofuran; hexane / -78 °C

1.2: 82 percent / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / -78 - 20 °C

2.1: 90 percent / DIBALH / diethyl ether; hexane / -78 °C

3.1: 63 percent / TEA; methanesulfonyl chloride; 4-DMAP / benzene / 0 - 20 °C

4.1: 67 percent / 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline] / (CuOTf)2*C₆H₆ / CH₂Cl₂ / 0 - 20 °C

With dmap; n-butyllithium; TEA; diisobutylaluminium hydride; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline]; methanesulfonyl chloride; diisopropylamine; copper(I) trifluoromethanesulfonate benzene; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; benzene; 1.1: Metallation / 1.2: Alkylation / 2.1: Reduction / 3.1: Elimination / 4.1: Cycloaddition;

DOI:10.1021/jo9807417

Reference yield:

(±)-3-benzyltetrahydro-2H-pyran-2-one (32821-74-2) → (1R,6R,7S)-6-benzyl-7-carbethoxy-2-oxabicyclo[4.1.0]heptane (213137-46-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / DIBALH / diethyl ether; hexane / -78 °C

2: 63 percent / TEA; methanesulfonyl chloride; 4-DMAP / benzene / 0 - 20 °C

3: 67 percent / 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline] / (CuOTf)2*C₆H₆ / CH₂Cl₂ / 0 - 20 °C

With dmap; TEA; diisobutylaluminium hydride; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline]; methanesulfonyl chloride; copper(I) trifluoromethanesulfonate benzene; In diethyl ether; hexane; dichloromethane; benzene; 1: Reduction / 2: Elimination / 3: Cycloaddition;

DOI:10.1021/jo9807417

upstream raw materials:

diazoacetic acid ethyl ester

5-benzyl-3,4-dihydro-2H-pyran

3,4,5,6-tetrahydro-2H-pyran-2-one

(±)-3-benzyltetrahydro-2H-pyran-2-one