ALLYL D-GLUCURONATE

Base Information

• Chemical Name: ALLYL D-GLUCURONATE
• CAS No.: 698358-03-1
• Molecular Formula: C₉H₁₄O₇
• Molecular Weight: 234.206
• Mol file: 698358-03-1.mol

Synonyms:ALLYL D-GLUCURONATE;alpha-D-Glucopyranuronic acid 2-propenyl ester

Chemical Property of ALLYL D-GLUCURONATE

Chemical Property:

• PSA: 124.29000
• LogP: -2.64190
• Storage Temp.: Amber Vial, -86°C Freezer, Under inert atmosphere
• Solubility.: Acetonitrile (Slightly), Methanol (Slightly), Water (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

Allyl D-glucuronate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: It is used in efficient synthesis of 1β-O-acyl glucuronides via regioselective acylation of allyl or benzyl D-glucuronate.Αcyl glucuronides are known metabolites of important drugs.

Technology Process of ALLYL D-GLUCURONATE

There total 10 articles about ALLYL D-GLUCURONATE 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: 79.0%

D-glucuronic acid (6556-12-3,489-91-8,528-16-5,552-12-5,577-46-8,643-33-4,2240-07-5,6294-16-2,10133-02-5,18402-78-3,18968-14-4,21179-08-8,23018-83-9,33599-45-0,33599-46-1,46171-67-9,46171-69-1,46172-26-3,70021-34-0,71031-08-8,104195-06-4,106499-29-0,124817-72-7) + allyl bromide (106-95-6) → allyl (2S,3S,4S,5R)-3,4,5,6-tetrahydroxytetrahydropyran-2-carboxylate (1070166-78-7,698358-03-1)

Guidance literature:

D-glucuronic acid; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 20 ℃; for 0.25h;

allyl bromide; In N,N-dimethyl-formamide;

DOI:10.1021/jo0612675

Reference yield: 43.0%

D-glucuronic acid (489-91-8,528-16-5,552-12-5,577-46-8,643-33-4,2240-07-5,6294-16-2,10133-02-5,18402-78-3,18968-14-4,21179-08-8,23018-83-9,33599-45-0,33599-46-1,46171-67-9,46171-69-1,46172-26-3,70021-34-0,71031-08-8,104195-06-4,106499-29-0,124817-72-7) + allyl bromide (106-95-6) → allyl (2S,3S,4S,5R,6R)-3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-carboxylate (698358-03-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

Reference yield: 34.0%

galacturonic acid (912483-14-8) + allyl bromide (106-95-6) → allyl glucuronate (698358-03-1)

Guidance literature:

With polymer-supported fluoride; In N,N-dimethyl-formamide; at 52 ℃; Inert atmosphere;

DOI:10.1002/jlcr.1607

upstream raw materials:

D-glucuronic acid

allyl bromide

D-Glucuronic acid

D-glucuronic acid

Downstream raw materials:

rhein acyl glucuronide

1-O-({trans-4-[4-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)phenyl]cyclohexyl}acetyl)-β-D-glucopyranuronic acid

allyl 6-([4-([1-(tert-butyl)-1,1-dimethylsilyl]oxymethyl)anilino]carbonyloxy)-3,4,5-trihydroxytetrahydro-2H-2-pyrancarboxylate