Benzyl Alcohol Glucuronide

Base Information

• Chemical Name: Benzyl Alcohol Glucuronide
• CAS No.: 5285-02-9
• Molecular Formula: C₁₃H₁₆O₇
• Molecular Weight: 284.266
• DSSTox Substance ID: DTXSID80430846
• Nikkaji Number: J1.649.283C
• Wikidata: Q82244573
• Mol file: 5285-02-9.mol

Synonyms:Benzyl Alcohol Glucuronide;5285-02-9;benzyl beta-d-glucopyranosiduronic acid;(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-phenylmethoxyoxane-2-carboxylic acid;(2S,3S,4S,5R,6R)-6-(Benzyloxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid;Benzyl |A-D-Glucopyranosiduronic Acid;SCHEMBL3492499;DTXSID80430846;(2S,3S,4S,5R,6R)-6-(BENZYLOXY)-3,4,5-TRIHYDROXYOXANE-2-CARBOXYLIC ACID

Chemical Property of Benzyl Alcohol Glucuronide

Chemical Property:

• Melting Point: 75-108 °C
• Boiling Point: 535.1±50.0 °C(Predicted)
• PKA: 2.83±0.70(Predicted)
• PSA: 116.45000
• Density: 1.50±0.1 g/cm3(Predicted)
• LogP: -0.90460
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 284.08960285
• Heavy Atom Count: 20
• Complexity: 329

Purity/Quality:

98% ^*data from raw suppliers

Benzylβ-D-GlucopyranosiduronicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC2C(C(C(C(O2)C(=O)O)O)O)O
• Isomeric SMILES: C1=CC=C(C=C1)CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C(=O)O)O)O)O

Technology Process of Benzyl Alcohol Glucuronide

There total 7 articles about Benzyl Alcohol Glucuronide 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:

(2S,3S,4S,5R)-6-Benzyloxy-3,4,5-tris-(1-ethoxy-ethoxy)-tetrahydro-pyran-2-carboxylic acid 1-ethoxy-ethyl ester (74801-10-8,74801-15-3) → Benzyl alcohol glucuronide (5285-02-9)

Guidance literature:

With triethylamine; In methanol; water; at 22 ℃; for 72h;

DOI:10.1016/S0008-6215(00)85373-2

Reference yield:

1-deoxy-1-fluoro-α-D-glucose (2106-10-7) → Benzyl alcohol glucuronide (5285-02-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hypochlorite; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hydroxide / water / 3 h / 4 °C / pH 9.5

2: histidine-6 tagged glucuronylsynthase E₅₀₄G mutant from Escherichia coli strain GMS₄₀₇(DE₃) / 21 °C / pH 7.5 / aq. phosphate buffer; Enzymatic reaction

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; histidine-6 tagged glucuronylsynthase E₅₀₄G mutant from Escherichia coli strain GMS₄₀₇(DE₃); sodium hydroxide; In water;

DOI:10.1021/jo101914s

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → Benzyl alcohol glucuronide (5285-02-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 4.6 g / silver carbonate / 6 h

2: saponification

With silver carbonate;

DOI:10.1016/S0008-6215(00)85373-2

upstream raw materials:

O¹-benzyl-β-D-glucopyranuronic acid methyl ester

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

methyl (benzyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate

benzyl alcohol

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

Refernces

• 1、 -. "TISSUE DEGENERATION PROTECTION". . . Retrieved 2010/05/13.