(3,4-Dibenzoyloxy-5-methoxyoxolan-2-yl)methyl benzoate

Base Information

• Chemical Name: (3,4-Dibenzoyloxy-5-methoxyoxolan-2-yl)methyl benzoate
• CAS No.: 7473-42-9
• Molecular Formula: C₂₇H₂₄O₈
• Molecular Weight: 476.483
• NSC Number: 400281,170260
• DSSTox Substance ID: DTXSID10962701
• ChEMBL ID: CHEMBL1454160
• Mol file: 7473-42-9.mol

Synonyms:(3,4-dibenzoyloxy-5-methoxyoxolan-2-yl)methyl benzoate;Methyl 2,3,5-tri-O-benzoylpentofuranoside;42793-97-5;SMR000589003;Methyl 2,3,5-tri-O-benzoyl-alpha-D-arabinoside;Methyl 2,3,5-tri-O-benzoylpentofuranoside #;(3,4-DIBENZOYLOXY-5-METHOXY-OXOLAN-2-YL)METHYL BENZOATE;MLS001174194;MLS003911813;CHEMBL1454160;SCHEMBL13146114;DTXSID10962701;XJKNQPQTQXKNOC-UHFFFAOYSA-N;HMS2872E03;Methyl .beta.-d-riboside tribenzoate;NSC170260;NSC400281;AKOS001046004;AKOS016879862;NSC-170260;NSC-400281;FT-0672258;methyl 2,3,5-tri-o-benzoyl-alpha-d-arabinofuranoside;Z56872192

Chemical Property of (3,4-Dibenzoyloxy-5-methoxyoxolan-2-yl)methyl benzoate

Chemical Property:

• Vapor Pressure: 2.68E-14mmHg at 25°C
• Melting Point: 98-100oC
• Boiling Point: 598.8°Cat760mmHg
• Flash Point: 256.1°C
• PSA: 97.36000
• Density: 1.32g/cm³
• LogP: 3.66590
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Very Slightly, Heated)
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 11
• Exact Mass: 476.14711772
• Heavy Atom Count: 35
• Complexity: 706

Purity/Quality:

99% ^*data from raw suppliers

Methyl 2,3,5-tri-O-benzoyl-a-D-arabinofuranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(C(O1)COC(=O)C2=CC=CC=C2)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4
• Uses: Used in the preparation of 1-α- and 1-β-D-Arabinofuranosyl-2-nitroimidazole (α-AZA and β-AZA) as synthons for a number of potential markers of tissue hypoxia. Methyl-2,3,5-tri-O-benzoyl-alpha-D-arabinofuranoside is used in the preparation of 1-α- and 1-β-D-Arabinofuranosyl-2-nitroimidazole (α-AZA and β-AZA) as synthons for a number of potential markers of tissue hypoxia.

Technology Process of (3,4-Dibenzoyloxy-5-methoxyoxolan-2-yl)methyl benzoate

There total 11 articles about (3,4-Dibenzoyloxy-5-methoxyoxolan-2-yl)methyl benzoate 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: 54.0%

methanol (67-56-1) + D-Arabinose (10323-20-3) + benzoyl chloride (98-88-4) → methyl tri-O-benzoyl-α-D-arabinofuranoside (7473-42-9,22861-07-0,38837-17-1,42793-97-5,52783-53-6,52783-87-6,69350-76-1,69927-20-4,84518-41-2,103238-80-8,105309-18-0,109959-28-6,109959-29-7,114923-83-0,120964-98-9)

Guidance literature:

methanol; D-Arabinose; With acetyl chloride; at 20 ℃;

benzoyl chloride; With pyridine; at 20 ℃; Cooling with ice;

DOI:10.1039/c3cc00042g

Reference yield: 51.1%

benzoyl chloride (98-88-4) + methyl D-arabinofuranoside (56607-40-0) → methyl tri-O-benzoyl-α-D-arabinofuranoside (7473-42-9,22861-07-0,38837-17-1,42793-97-5,52783-53-6,52783-87-6,69350-76-1,69927-20-4,84518-41-2,103238-80-8,105309-18-0,109959-28-6,109959-29-7,114923-83-0,120964-98-9)

Guidance literature:

With pyridine; at 0 - 55 ℃; for 1.5h;

DOI:10.1002/(SICI)1099-1344(199707)39:7<541::AID-JLCR5>3.0.CO;2-B

Reference yield:

benzoyl chloride (98-88-4) + methyl D-arabinofuranoside (79083-42-4) → methyl 2,3,5-tri-O-benzoyl-β-D-arabinofuranoside + methyl tri-O-benzoyl-α-D-arabinofuranoside (7473-42-9,22861-07-0,38837-17-1,42793-97-5,52783-53-6,52783-87-6,69350-76-1,69927-20-4,84518-41-2,103238-80-8,105309-18-0,109959-28-6,109959-29-7,114923-83-0,120964-98-9)

Guidance literature:

With pyridine; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol400931p

upstream raw materials:

methanol

D-Arabinose

benzoyl chloride

tri-O-benzoyl-β-D-arabinofuranosyl bromide

Downstream raw materials:

tri-O-benzoyl-β-D-arabinofuranosyl bromide

2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl bromide

1-(α-D-arabinofuranosyl)-2-aminoimidazole

1-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2-acetamidoimidazole

Refernces

• 1、 Kandasamy, Jeyakumar,Hurevich, Mattan,Seeberger, Peter H.. "Automated solid phase synthesis of oligoarabinofuranosides". supporting information. p. 4453 - 4455. Retrieved 2013/06/26.
• 2、 Ramamurty, Changalvala V. S.,Ganney, Parimala,Rao, C. Srinivas,Fraser-Reid, Bert. "Ready preparation of furanosyl n-pentenyl orthoesters from corresponding methyl furanosides". supporting information; experimental part. p. 2245 - 2247. Retrieved 2011/05/17.