(1S,3R,4R,5R)-3-benzyloxy-1,4-dihydroxycyclohexane-1,5-carbolactone

Base Information

• Chemical Name: (1S,3R,4R,5R)-3-benzyloxy-1,4-dihydroxycyclohexane-1,5-carbolactone
• CAS No.: 185810-83-7
• Molecular Formula: C₁₄H₁₆O₅
• Molecular Weight: 264.278
• Mol file: 185810-83-7.mol

Synonyms:(1S,3R,4R,5R)-3-benzyloxy-1,4-dihydroxycyclohexane-1,5-carbolactone

Chemical Property of (1S,3R,4R,5R)-3-benzyloxy-1,4-dihydroxycyclohexane-1,5-carbolactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R,4R,5R)-3-benzyloxy-1,4-dihydroxycyclohexane-1,5-carbolactone

There total 2 articles about (1S,3R,4R,5R)-3-benzyloxy-1,4-dihydroxycyclohexane-1,5-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:

D-(-)-quinic acid (77-95-2) → (1S,3R,4R,5R)-3-benzyloxy-1,4-dihydroxycyclohexane-1,5-carbolactone (185810-83-7)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH / toluene

2: Bu₂SnO

With di(n-butyl)tin oxide; toluene-4-sulfonic acid; In toluene; 1: Lactonization / 2: Metallation / 2: Benzylation;

DOI:10.1016/S0960-894X(00)00021-4

Reference yield:

benzyl bromide (100-39-0) + 1,5-quinide (665-27-0) → (1S,3R,4R,5R)-3-benzyloxy-1,4-dihydroxycyclohexane-1,5-carbolactone (185810-83-7)

Guidance literature:

With di(n-butyl)tin oxide; Yield given. Multistep reaction; 1.) DMF, benzene, reflux, 4h, 2.) DMF, benzene, reflux, 6 h;

DOI:10.1021/jo961713w

Reference yield: 97.0%

t-butyldimethylsiyl triflate (69739-34-0) + (1S,3R,4R,5R)-3-benzyloxy-1,4-dihydroxycyclohexane-1,5-carbolactone (185810-83-7) → (1S,3R,4R,5R)-3-benzyloxy-1,4-bis(tert-butyldimethylsilyloxy)cyclohexane-1,5-carbolactone (862791-08-0)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1021/jm0501836

upstream raw materials:

benzyl bromide

1,5-quinide

D-(-)-quinic acid

Downstream raw materials:

(1S,3R,4R,5R)-3-Benzyloxy-1,4-dimethoxy-6-oxa-bicyclo[3.2.1]octan-7-one

(1S,3R,4R,5R)-3-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-6-oxa-bicyclo[3.2.1]octan-7-one

(1S,3R,4R,5R)-3-benzyloxy-1,4-bis(tert-butyldimethylsilyloxy)cyclohexane-1,5-carbolactone

(1R,3R,4R)-1,4-dihydroxy-5-phenylcyclohex-5-ene-1,3-carbolactone