UVARIGRANOL E

Base Information

• Chemical Name: UVARIGRANOL E
• CAS No.: 176598-10-0
• Molecular Formula: C₂₃H₂₂O₈
• Molecular Weight: 426.423
• Mol file: 176598-10-0.mol

Synonyms:5-Cyclohexene-1,2,3,4-tetrol,2-[(acetyloxy)methyl]-, 1,4-dibenzoate, [1S-(1a,2b,3b,4a)]-; (+)-Uvarigranol E; Uvarigranol E

Chemical Property of UVARIGRANOL E

Chemical Property:

• PSA: 119.36000
• Density: 1.37±0.1 g/cm3 (20 oC 760 Torr)
• LogP: 1.66250

Purity/Quality:

≥98% ^*data from raw suppliers

UvarigranolE ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of UVARIGRANOL E

There total 6 articles about UVARIGRANOL E 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: 80.0%

(3aR,4S,7R,7aS)-3a-(acetoxymethyl)-2,2-dimethyl-3a,4,7,7a-tetrahydrobenzo[d][1,3]dioxole-4,7-diyl dibenzoate → (1R,4S,5S,6S)-5-(acetoxymethyl)-5,6-dihydroxycyclohex-2-ene-1,4-diyl dibenzoate (176598-10-0)

Guidance literature:

With water; trifluoroacetic acid; at 20 ℃; for 5h;

DOI:10.1016/j.carres.2021.108432

Reference yield:

C26H34O5Si → (1R,4S,5S,6S)-5-(acetoxymethyl)-5,6-dihydroxycyclohex-2-ene-1,4-diyl dibenzoate (176598-10-0)

Guidance literature:

Multi-step reaction with 6 steps

1: tetrahydrofuran / 12 h / -78 - 20 °C / Inert atmosphere

2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 12 h / Reflux

3: triethylamine; dmap / dichloromethane / 2 h / 0 - 20 °C

4: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 1 h / 0 °C

5: triethylamine; dmap / dichloromethane / 6 h / 0 - 20 °C

6: trifluoroacetic acid; water / 5 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; tetrabutyl ammonium fluoride; water; acetic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/j.carres.2021.108432

Reference yield:

benzoyl chloride (98-88-4) → (1R,4S,5S,6S)-5-(acetoxymethyl)-5,6-dihydroxycyclohex-2-ene-1,4-diyl dibenzoate (176598-10-0)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine; dmap / dichloromethane / 2 h / 0 - 20 °C

2: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 1 h / 0 °C

3: triethylamine; dmap / dichloromethane / 6 h / 0 - 20 °C

4: trifluoroacetic acid; water / 5 h / 20 °C

With dmap; tetrabutyl ammonium fluoride; water; acetic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.carres.2021.108432

upstream raw materials:

benzoyl chloride