Benzyl |A-D-Glucopyranosiduronic Acid Methyl Ester Triacetate

Base Information

• Chemical Name: Benzyl |A-D-Glucopyranosiduronic Acid Methyl Ester Triacetate
• CAS No.: 3080-47-5
• Molecular Formula: C20H24O10
• Molecular Weight: 424.405
• DSSTox Substance ID: DTXSID50443600
• Nikkaji Number: J1.577.260C
• Wikidata: Q82261491
• Mol file: 3080-47-5.mol

Synonyms:3080-47-5;Benzyl |A-D-Glucopyranosiduronic Acid Methyl Ester Triacetate;methyl (2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-phenylmethoxyoxane-2-carboxylate;BENZYL BETA-D-GLUCOPYRANOSIDURONIC ACID METHYL ESTER TRIACETATE;DTXSID50443600;IQZIUMCUDYOPQO-KVIJGQROSA-N;Benzyl ?-D-Glucopyranosiduronic Acid Methyl Ester Triacetate;1-O-Benzyl-2-O,3-O,4-O-triacetyl-beta-D-glucopyranuronic acid methyl ester

Chemical Property of Benzyl |A-D-Glucopyranosiduronic Acid Methyl Ester Triacetate

Chemical Property:

• Melting Point: 136-138°C
• Boiling Point: 478.0±45.0 °C(Predicted)
• PSA: 123.66000
• Density: 1.29±0.1 g/cm3(Predicted)
• LogP: 0.89620
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Ethyl Acetate
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 11
• Exact Mass: 424.13694696
• Heavy Atom Count: 30
• Complexity: 627

Purity/Quality:

98% ^*data from raw suppliers

Benzyl b-D-glucopyranosiduronic acid methyl ester triacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1C(C(OC(C1OC(=O)C)OCC2=CC=CC=C2)C(=O)OC)OC(=O)C
• Isomeric SMILES: CC(=O)O[C@H]1[C@@H]([C@H](O[C@H]([C@@H]1OC(=O)C)OCC2=CC=CC=C2)C(=O)OC)OC(=O)C
• Uses: Protected Glucopyranosiduronic Acid.

Technology Process of Benzyl |A-D-Glucopyranosiduronic Acid Methyl Ester Triacetate

There total 5 articles about Benzyl |A-D-Glucopyranosiduronic Acid Methyl Ester Triacetate 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: 81.0%

benzyl alcohol (100-51-6,185532-71-2) + 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3) → methyl (benzyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate (3080-47-5)

Guidance literature:

With MS 4 Angstroem; silver(l) oxide; In toluene; for 20h; Ambient temperature;

DOI:10.1016/S0960-894X(97)00123-6

Reference yield: 57.0%

methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate (72692-06-9,73464-50-3,3082-95-9) + benzyl alcohol (100-51-6,185532-71-2) → methyl (benzyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate (3080-47-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 0 ℃; for 0.416667h;

DOI:10.1021/jo00199a046

Reference yield: 31.0%

methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate (72692-06-9,73464-50-3,3082-95-9) + benzyl bromide (100-39-0) → methyl (benzyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate (3080-47-5)

Guidance literature:

With silver carbonate; In toluene; at 20 ℃; Inert atmosphere; Darkness;

DOI:10.1002/cbic.201300547

upstream raw materials:

benzyl alcohol

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate

benzyl bromide

Downstream raw materials:

(2S,3S,4S,5R)-6-Benzyloxy-3,4,5-tris-(1-ethoxy-ethoxy)-tetrahydro-pyran-2-carboxylic acid 1-ethoxy-ethyl ester

(2S,3S,4S,5R,6R)-6-{2-[2-(4-Chloro-phenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl]-acetoxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid

Licofelone glucuronide

2,2,2-trichloroethyl (benzyl 2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranosid)uronate

Refernces

• 1、 Jongkees, Seino A. K.,Yoo, Hayoung,Withers, Stephen G.. "Mechanistic insights from substrate preference in unsaturated glucuronyl hydrolase". . p. 124 - 134. Retrieved 2014/01/06.
• 2、 Madec-Lougerstay, Rachel,Florent, Jean-Claude,Monneret, Claude. "Synthesis of self-immolative glucuroenide spacers based on aminomethylcarbamate. Application to 5-fluorouracil prodrugs for antibody-directed enzyme prodrug therapy". . p. 1369 - 1375. Retrieved 2007/10/03.