2,3,5-Tri-O-benzoyl-alpha-D-arabinofuranosyl bromide

Base Information

• Chemical Name: 2,3,5-Tri-O-benzoyl-alpha-D-arabinofuranosyl bromide
• CAS No.: 4348-68-9
• Molecular Formula: C26H21 Br O7
• Molecular Weight: 525.353
• Hs Code.: 2932190090
• DSSTox Substance ID: DTXSID80451975
• Nikkaji Number: J938.058B
• Mol file: 4348-68-9.mol

Synonyms:4348-68-9;2,3,5-Tri-O-benzoyl-alpha-D-arabinofuranosyl bromide;[(2R,3R,4S,5R)-3,4-dibenzoyloxy-5-bromooxolan-2-yl]methyl benzoate;(2R,3R,4S,5R)-2-((Benzoyloxy)methyl)-5-bromotetrahydrofuran-3,4-diyl dibenzoate;2 3 5-TRI-O-BENZOYL-alpha-D-ARABINO-FURA;2,3,5-Tri-O-benzoyl-a-D-arabinofuranosyl bromide;SCHEMBL3496162;DTXSID80451975;AKOS016024012;2,3,5-Tri-O-benzoyl--D-arabinosyl bromide;D96151;2,3,5-Tri-O-benzoyl- alpha -D-arabinofuranosyl bromide;2-O,3-O,5-O-Tribenzoyl-alpha-D-arabinofuranosyl bromide;2,3,5-Tri-O-benzoyl-alpha-D-arabinofuranosyl bromide, >=96.0% (HPLC)

Chemical Property of 2,3,5-Tri-O-benzoyl-alpha-D-arabinofuranosyl bromide

Chemical Property:

• Vapor Pressure: 6.89E-15mmHg at 25°C
• Refractive Index: 1.636
• Boiling Point: 611.4°C at 760 mmHg
• Flash Point: 323.6°C
• PSA: 88.13000
• Density: 1.49g/cm³
• LogP: 4.41440
• Storage Temp.: 2-8°C
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 10
• Exact Mass: 524.04707
• Heavy Atom Count: 34
• Complexity: 695

Purity/Quality:

99%, ^*data from raw suppliers

2,3,5-Tri-O-benzoyl-a-D-arabinofuranosyl bromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)OCC2C(C(C(O2)Br)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4
• Isomeric SMILES: C1=CC=C(C=C1)C(=O)OC[C@@H]2[C@H]([C@@H]([C@H](O2)Br)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4

Technology Process of 2,3,5-Tri-O-benzoyl-alpha-D-arabinofuranosyl bromide

There total 8 articles about 2,3,5-Tri-O-benzoyl-alpha-D-arabinofuranosyl bromide 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: 27.4%

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) → 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl bromide (4348-68-9)

Guidance literature:

With hydrogen bromide; acetic acid; for 0.5h; Ambient temperature;

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

Reference yield:

D-Arabinose (10323-20-3) → 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl bromide (4348-68-9)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen chloride; pyridine

2: hydrogen bromide; acetic acid

With pyridine; hydrogenchloride; hydrogen bromide; acetic acid;

DOI:10.1021/ja01541a058

Reference yield:

benzoyl chloride (98-88-4) → 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl bromide (4348-68-9)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen chloride; pyridine

2: hydrogen bromide; acetic acid

With pyridine; hydrogenchloride; hydrogen bromide; acetic acid;

DOI:10.1021/ja01541a058

upstream raw materials:

methyl tri-O-benzoyl-α-D-arabinofuranoside

α-arabinofuranose

benzoyl chloride

D-arabinopyranose

Downstream raw materials:

3,5-di-O-benzoyl-1,2--α-D-ribofuranose

dibutyl (2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)phosphate

9-β-D-(2’,3’,5’-tri-O-benzoylarabinofuranosyl)-2,6-dichloropurine

3'-phenylpropyl 2,3,5-tri-O-benzoylarabinofuranoside

Refernces

• 1、 Khare, Naveen K.,Duarte, Franco J.,Reynolds, Robert C.,Maddry, Joseph A.. "Design, synthesis and activity of thio-linked arabinofuranosyl disaccharides against mycobacterial tuberculosis (MTB) and Mycobacterium avium complex (MAC)". . p. 290 - 315. Retrieved 2013/02/26.
• 2、 Abronina,Podvalnyy,Mel'Nikova,Zinin,Fedina,Kachala,Torgov,Kononov,Panfertsev,Baranova,Mochalov,Dyatlova,Biketov. "Synthesis of covalent conjugates of hexaarabinofuranoside with proteins and their testing as antigens for serodiagnosis of tuberculosis". scheme or table. p. 2333 - 2337. Retrieved 2011/09/13.