(10S,11R)-10,11-dihydroxy-10,11-dihydrosqualene 3-((S)-(+)-α-methoxy-α-phenyl)acetate

Base Information

• Chemical Name: (10S,11R)-10,11-dihydroxy-10,11-dihydrosqualene 3-((S)-(+)-α-methoxy-α-phenyl)acetate
• CAS No.: 819073-84-2
• Molecular Formula: C₃₉H₆₀O₄
• Molecular Weight: 592.903
• Mol file: 819073-84-2.mol

Synonyms:(10S,11R)-10,11-dihydroxy-10,11-dihydrosqualene 3-((S)-(+)-α-methoxy-α-phenyl)acetate

Chemical Property of (10S,11R)-10,11-dihydroxy-10,11-dihydrosqualene 3-((S)-(+)-α-methoxy-α-phenyl)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (10S,11R)-10,11-dihydroxy-10,11-dihydrosqualene 3-((S)-(+)-α-methoxy-α-phenyl)acetate

There total 5 articles about (10S,11R)-10,11-dihydroxy-10,11-dihydrosqualene 3-((S)-(+)-α-methoxy-α-phenyl)acetate 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: 42.0%

(6E,14E,18E)-2,6,10,15,19,23-hexamethyl-tetracosa-2,6,14,18,22-pentaene-10,11-diol (144641-00-9,153650-82-9) + (S)-2-methoxy-2-phenylacetic acid (26164-26-1) → (10R,11S)-10,11-dihydroxy-10,11-dihydrosqualene 3-((S)-(+)-α-methoxy-α-phenyl)acetate (819073-83-1) + (10S,11R)-10,11-dihydroxy-10,11-dihydrosqualene 3-((S)-(+)-α-methoxy-α-phenyl)acetate (819073-84-2)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 2h; Molecular sieve; Inert atmosphere;

DOI:10.1021/ol3016836

Reference yield:

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene (111-02-4) → (10S,11R)-10,11-dihydroxy-10,11-dihydrosqualene 3-((S)-(+)-α-methoxy-α-phenyl)acetate (819073-84-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.5 h / 0 °C

1.2: 2.5 h / 0 °C

2.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 20 °C / Molecular sieve; Inert atmosphere

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/ol3016836

Reference yield:

(S)-2-methoxy-2-phenylacetic acid (26164-26-1) + 10(R*),11(S*)-Dihydroxy-10,11-dihydrosqualene (153650-82-9) → (10R,11S)-10,11-dihydroxy-10,11-dihydrosqualene 3-((S)-(+)-α-methoxy-α-phenyl)acetate (819073-83-1) + (10S,11R)-10,11-dihydroxy-10,11-dihydrosqualene 3-((S)-(+)-α-methoxy-α-phenyl)acetate (819073-84-2)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2004.09.059

upstream raw materials:

(S)-2-methoxy-2-phenylacetic acid

10(R*),11(S*)-Dihydroxy-10,11-dihydrosqualene

(S)-(+)-O-methylmandeloyl chloride

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Downstream raw materials:

(10R,11R)-dihydroxysqualene