2(R)-endo-hydroxy-1(R),4(S)-cineole (S)-(+)-O-acetylmandelate

Base Information

• Chemical Name: 2(R)-endo-hydroxy-1(R),4(S)-cineole (S)-(+)-O-acetylmandelate
• CAS No.: 117306-77-1
• Molecular Formula: C₂₀H₂₆O₅
• Molecular Weight: 346.423
• Mol file: 117306-77-1.mol

Synonyms:2(R)-endo-hydroxy-1(R),4(S)-cineole (S)-(+)-O-acetylmandelate

Chemical Property of 2(R)-endo-hydroxy-1(R),4(S)-cineole (S)-(+)-O-acetylmandelate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2(R)-endo-hydroxy-1(R),4(S)-cineole (S)-(+)-O-acetylmandelate

There total 4 articles about 2(R)-endo-hydroxy-1(R),4(S)-cineole (S)-(+)-O-acetylmandelate 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: 70.0%

2(R)-endo-hydroxy-1,4-cineole (22555-57-3,22621-68-7,38630-76-1,50302-07-3,87172-89-2,96645-97-5,103834-29-3,107133-87-9,111955-86-3) + (S)-acetylmandelic acid (7322-88-5) → 2(R)-endo-hydroxy-1(R),4(S)-cineole (S)-(+)-O-acetylmandelate (117306-77-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃;

DOI:10.1021/jo00259a017

Reference yield:

1,4-cineole (470-67-7) → 2(R)-endo-hydroxy-1(R),4(S)-cineole (S)-(+)-O-acetylmandelate (117306-77-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 h / Streptomyces griseus; microbiological hydroxylation

2: 70 percent / N,N-dicyclohexylcarbodiimide, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 0 °C

With dmap; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1021/jo00259a017

Reference yield:

2-exo-hydroxy-1-methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane (22555-57-3) → 2(R)-endo-hydroxy-1(R),4(S)-cineole (S)-(+)-O-acetylmandelate (117306-77-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / 1.) oxalyl chloride, DMSO, 2.) Et₃N / CH₂Cl₂ / 1.) -60 deg C, 20 min, 2.) from -60 deg C to RT

2: 60 percent / NaBH₄ / methanol / 0.67 h / Ambient temperature

3: 70 percent / N,N-dicyclohexylcarbodiimide, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 0 °C

With dmap; sodium tetrahydroborate; oxalyl dichloride; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; In methanol; dichloromethane;

DOI:10.1021/jo00259a017

upstream raw materials:

2(R)-endo-hydroxy-1,4-cineole

(S)-acetylmandelic acid

1,4-cineole

2-exo-hydroxy-1-methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane

Refernces