(3R,4R,5R)-3-benzoyloxy-4,5-dihydroxycyclohexanone 4,5-O-cyclohexylidene acetal

Base Information

• Chemical Name: (3R,4R,5R)-3-benzoyloxy-4,5-dihydroxycyclohexanone 4,5-O-cyclohexylidene acetal
• CAS No.: 77003-54-4
• Molecular Formula: C₁₉H₂₂O₅
• Molecular Weight: 330.381
• Mol file: 77003-54-4.mol

Synonyms:(3R,4R,5R)-3-benzoyloxy-4,5-dihydroxycyclohexanone 4,5-O-cyclohexylidene acetal

Chemical Property of (3R,4R,5R)-3-benzoyloxy-4,5-dihydroxycyclohexanone 4,5-O-cyclohexylidene acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5R)-3-benzoyloxy-4,5-dihydroxycyclohexanone 4,5-O-cyclohexylidene acetal

There total 5 articles about (3R,4R,5R)-3-benzoyloxy-4,5-dihydroxycyclohexanone 4,5-O-cyclohexylidene acetal 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: 92.0%

3-O,4-O-cyclohexylidene-(3R,4S,5R)-trihydroxycyclohexan-1-one (53397-93-6) + benzoyl chloride (98-88-4) → (3R,4R,5R)-3-benzoyloxy-4,5-dihydroxycyclohexanone 4,5-O-cyclohexylidene acetal (77003-54-4)

Guidance literature:

In pyridine;

Reference yield:

D-(-)-quinic acid (77-95-2) → (3R,4R,5R)-3-benzoyloxy-4,5-dihydroxycyclohexanone 4,5-O-cyclohexylidene acetal (77003-54-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / conc. sulphuric acid / 1 h / Heating

2: NaBH₄ / ethanol / 12 h

3: 82 percent / sodium periodate / ethanol; H₂O / 0.25 h

4: 90 percent / pyridine / 1.) cooling with CCl₄-solid CO₂, 25 min, 2.) room temperature, overnight

With sodium tetrahydroborate; sodium periodate; sulfuric acid; In pyridine; ethanol; water;

Reference yield:

(-)-4,5-cyclohexylidenequinic acid lactone (35949-53-2) → (3R,4R,5R)-3-benzoyloxy-4,5-dihydroxycyclohexanone 4,5-O-cyclohexylidene acetal (77003-54-4)

Guidance literature:

Multi-step reaction with 3 steps

1: NaBH₄ / ethanol / 12 h

2: 82 percent / sodium periodate / ethanol; H₂O / 0.25 h

3: 90 percent / pyridine / 1.) cooling with CCl₄-solid CO₂, 25 min, 2.) room temperature, overnight

With sodium tetrahydroborate; sodium periodate; In pyridine; ethanol; water;

upstream raw materials:

3-O,4-O-cyclohexylidene-(3R,4S,5R)-trihydroxycyclohexan-1-one

benzoyl chloride

D-(-)-quinic acid

(-)-4,5-cyclohexylidenequinic acid lactone

Downstream raw materials:

4-(2-hydroxyethoxy)-phenol

(7R,8R,9R)-9-benzoyloxy-7,8-dihydroxy-1,4-dioxaspiro<4.5>decane

(7R,8R,9R)-9-benzoyloxy-7,8-O-cyclohexylidene-7,8-dihydroxy-1,4-dioxaspiro<4.5>decane

(7R,8R,9R)-9-benzoyloxy-7,8-dihydroxy-1,4-dithiaspiro<4.5>decane