2-Deoxy-2-fluoro-alpha-D-arabinofuranosyl bromide 3,5-dibenzoate

Base Information

Chemical Name:2-Deoxy-2-fluoro-alpha-D-arabinofuranosyl bromide 3,5-dibenzoate
CAS No.:97614-44-3
Molecular Formula:C19H16BrFO5
Molecular Weight:423.235
Hs Code.:2938909090
DSSTox Substance ID:DTXSID80458186
Nikkaji Number:J651.513D
Wikidata:Q72462147
Mol file:97614-44-3.mol

Synonyms:97614-44-3;2-Deoxy-2-fluoro-alpha-D-arabinofuranosyl bromide 3,5-dibenzoate;[(2R,3R,4S,5R)-3-benzoyloxy-5-bromo-4-fluorooxolan-2-yl]methyl benzoate;((2R,3R,4S,5R)-3-(Benzoyloxy)-5-bromo-4-fluorotetrahydrofuran-2-yl)methyl benzoate;[(2R,3R,4S,5R)-3-Benzoyloxy-5-bromo-4-fluoro-tetrahydrofuran-2-yl]methyl benzoate;SCHEMBL1357298;DTXSID80458186;MFCD15144963;[(2R,3R,4S,5R)-3-(Benzoyloxy)-5-bromo-4-fluorooxolan-2-yl]methyl benzoate;AKOS022178768;BS-33426;CS-0130700;H11804;2-Deoxy-2-fluoro-alpha-D-arabinofuranosylbromide3,5-dibenzoate;2-deoxy-2-fluoro-3,5-di-o-benzoyl-alpha-d-arabinofuranosyl bromide;3,5-di-O-benzoyl-2-deoxy-2-fluoro-alpha-D-arabinofuranosyl bromide;2-Deoxy-2-fluoro-3-O,5-O-dibenzoyl-alpha-D-arabinofuranosyl bromide

Suppliers and Price of 2-Deoxy-2-fluoro-alpha-D-arabinofuranosyl bromide 3,5-dibenzoate

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 18 raw suppliers

Chemical Property of 2-Deoxy-2-fluoro-alpha-D-arabinofuranosyl bromide 3,5-dibenzoate

Chemical Property:

Melting Point:73℃
Boiling Point:492.3±45.0 °C(Predicted)
PSA：61.83000
Density:1.51
LogP:3.52690
XLogP3:4.4
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:7
Exact Mass:422.01651
Heavy Atom Count:26
Complexity:490

Purity/Quality:: 98% ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:C1=CC=C(C=C1)C(=O)OCC2C(C(C(O2)Br)F)OC(=O)C3=CC=CC=C3
Isomeric SMILES:C1=CC=C(C=C1)C(=O)OC[C@@H]2[C@H]([C@@H]([C@H](O2)Br)F)OC(=O)C3=CC=CC=C3
Uses antibiotic related to gentomycin 2-Deoxy-2-fluoro-α-D-arabinofuranosyl Bromide 3,5-Dibenzoate, can be used in the synthesis of Clofarabine (C586890), which is a second generation purine nucleoside analog. It is also an antimetabolite that inhibits DNA synthesis and resists deamination by adenosine deaminase. Antineoplastic.

Technology Process of 2-Deoxy-2-fluoro-alpha-D-arabinofuranosyl bromide 3,5-dibenzoate

There total 8 articles about 2-Deoxy-2-fluoro-alpha-D-arabinofuranosyl bromide 3,5-dibenzoate 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: 100.0%

: 97614-43-2
1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

: 97614-44-3
2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide

Guidance literature:: With hydrogen bromide; acetic acid; In dichloromethane; at -5 - 20 ℃; for 18.33h; Inert atmosphere;

Reference yield: 100.0%

: (3S,4R,5R)-5-((benzoyloxy)methyl)-3-fluorotetrahydrofuran-2,4-diyl dibenzoate

: 97614-44-3
2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide

Guidance literature:: With hydrogen bromide; acetic acid; In dichloromethane; at 0 - 20 ℃; for 12h; Inert atmosphere;
DOI:10.1039/c9ob01515a

Reference yield:

: 22224-41-5
1,3,5-tri-O-benzoyl-α-D-ribofuranoside

: 97614-44-3
2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide

Guidance literature:: Multi-step reaction with 2 steps

1: 83 percent / [bis(2-methoxyethyl)amino]sulfur trifluoride / CH₂Cl₂ / 50 °C

2: 90 percent / HBr / CH₂Cl₂ / 24 h / 20 °C

With hydrogen bromide; (bis-(2-methoxyethyl)amino)sulfur trufluoride; In dichloromethane;
DOI:10.1081/NCN-120022961