(1S,3R,4R,5R)-4,5-Benzylidenedioxy-1-hydroxycyclohexane-1,3-carbolactone

Base Information

• Chemical Name: (1S,3R,4R,5R)-4,5-Benzylidenedioxy-1-hydroxycyclohexane-1,3-carbolactone
• CAS No.: 32384-44-4
• Molecular Formula: C₁₄H₁₄O₅
• Molecular Weight: 262.262
• Mol file: 32384-44-4.mol

Synonyms:(1S,3R,4R,5R)-4,5-Benzylidenedioxy-1-hydroxycyclohexane-1,3-carbolactone

Chemical Property of (1S,3R,4R,5R)-4,5-Benzylidenedioxy-1-hydroxycyclohexane-1,3-carbolactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R,4R,5R)-4,5-Benzylidenedioxy-1-hydroxycyclohexane-1,3-carbolactone

There total 3 articles about (1S,3R,4R,5R)-4,5-Benzylidenedioxy-1-hydroxycyclohexane-1,3-carbolactone 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: 90.0%

D-(-)-quinic acid (77-95-2) + benzaldehyde (100-52-7) → (1S,3R,4R,5R)-4,5-Benzylidenedioxy-1-hydroxycyclohexane-1,3-carbolactone (32384-44-4)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; Heating;

DOI:10.1002/mrc.1260270607

Reference yield:

benzaldehyde (100-52-7) + (1R,3R,4S)-1,3,4,5-Tetrahydroxy-cyclohexanecarboxylic acid (77-95-2) → (1S,3R,5RS,7R,8R)-5-phenyl-10-oxo-4,6,9-trioxatricyclo<6.2.11,8.03,7>undecan-1-ol (32384-44-4,92282-37-6,94903-42-1)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 12h; Yield given; Heating;

DOI:10.1021/jo00206a035

Reference yield:

D-(-)-quinic acid (77-95-2) + benzaldehyde (100-52-7) → (1S,3R,4R,5R)-4,5-Benzylidenedioxy-1-hydroxycyclohexane-1,3-carbolactone (32384-44-4) + (1R,2R,4R,6R,8S)-8-Hydroxy-4-phenyl-3,5,10-trioxa-tricyclo[6.2.1.02,6]undecan-9-one (94903-42-1)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 22h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Heating;

DOI:10.1039/p19960002371

upstream raw materials:

benzaldehyde

(1R,3R,4S)-1,3,4,5-Tetrahydroxy-cyclohexanecarboxylic acid

D-(-)-quinic acid

Downstream raw materials:

(1S,2R,4R,6R,8S)-4-(methoxycarbonyl)-8-phenyl-7,9-dioxabicyclo<4.3.0>nonane-2,4-diol

(3R,4R,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid

(1S,4S,6R,8S)-4-(methoxycarbonyl)-2-oxo-8-phenyl-7,9-dioxabicyclo<4.3.0>nonan-4-ol

(1R,2R,6R,8S)-2-(benzoyloxy)-4-(methoxycarbonyl)-8-phenyl-7,9-dioxabicyclo<4.3.0>non-3-ene