(+)-(1R,6R)-1-ethynyl-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptane

Base Information

• Chemical Name: (+)-(1R,6R)-1-ethynyl-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptane
• CAS No.: 849413-73-6
• Molecular Formula: C₁₁H₁₆O
• Molecular Weight: 164.247
• Mol file: 849413-73-6.mol

Synonyms:(+)-(1R,6R)-1-ethynyl-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptane

Chemical Property of (+)-(1R,6R)-1-ethynyl-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(1R,6R)-1-ethynyl-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptane

There total 5 articles about (+)-(1R,6R)-1-ethynyl-2,2,6-trimethyl-7-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: 84.0%

(-)-(1S,6R)-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptane-1-carbaldehyde (88852-23-7) + diazomethyl-trimethyl-silane (18107-18-1) → (+)-(1R,6R)-1-ethynyl-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptane (849413-73-6)

Guidance literature:

diazomethyl-trimethyl-silane; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 1h;

(-)-(1S,6R)-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptane-1-carbaldehyde; In tetrahydrofuran; at 25 ℃; for 2h;

DOI:10.1055/s-2004-837214

Reference yield:

β-cyclogeraniol (472-20-8) → (+)-(1R,6R)-1-ethynyl-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptane (849413-73-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 98 percent / Ti(OiPr)4; diethyl (-)-D-tartrate; tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 12 h / -20 °C

2.1: 89 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -60 - 25 °C

3.1: iPr₂NH; nBuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.2: 84 percent / tetrahydrofuran; hexane / 3 h / -78 - 25 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; oxalyl dichloride; diethyl (2S,3S)-tartrate; dimethyl sulfoxide; triethylamine; diisopropylamine; In tetrahydrofuran; 2,2,4-trimethylpentane; hexane; dichloromethane; 1.1: Sharpless asymmetric epoxidation / 2.1: Swern oxidation / 3.1: Colvin reaction;

DOI:10.1002/chem.200600959

Reference yield:

(E)-3-(2,6,6-Trimethyl-cyclohex-1-enyl)-acrylic acid methyl ester (15356-72-6) → (+)-(1R,6R)-1-ethynyl-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptane (849413-73-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: O₃ / methanol / 2.5 h / -78 °C

1.2: 93 percent / Zn; AcOH / H₂O

2.1: 76 percent / NaBH₄ / methanol / 13 h / 0 - 25 °C

3.1: 67 percent / tBuOOH; Ti(OiPr)4; (-)-diisopropyl tartrate / molecular sieves 4 Angstroem / CH₂Cl₂ / 12 h / -25 °C

4.1: 99 percent / (COCl)2; dimethyl sulfoxide; Et₃N / 1 h / -78 °C

5.1: 57 percent / lithium diisopropylamide / 0.5 h / -78 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; oxalyl dichloride; (-)-diisopropyl tartrate; ozone; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; 4 A molecular sieve; In methanol; dichloromethane; 3.1: asymmetric Sharpless epoxidation / 4.1: Swern oxidation;

DOI:10.1002/anie.200460259

upstream raw materials:

(-)-(1S,6R)-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptane-1-carbaldehyde

diazomethyl-trimethyl-silane

β-cyclogeraniol

(+)-[(1R,6R)-2,2,6-trimethyl-7-oxa-bicyclo[4.1.0]heptan-1-yl]methanol