2-Bromo-2-deoxy-5-methyluridine-3,5-diacetate

Base Information

• Chemical Name: 2-Bromo-2-deoxy-5-methyluridine-3,5-diacetate
• CAS No.: 95585-76-5
• Molecular Formula: C10H13 Br N2 O5
• Molecular Weight: 321.128
• Mol file: 95585-76-5.mol

Synonyms:Thymidine,2'-bromo- (7CI)

Chemical Property of 2-Bromo-2-deoxy-5-methyluridine-3,5-diacetate

Chemical Property:

• PSA: 104.81000
• LogP: -0.72860

Purity/Quality:

97% ^*data from raw suppliers

2'-DEOXY-2'-BROMO-THYMIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Bromo-2-deoxy-5-methyluridine-3,5-diacetate

There total 8 articles about 2-Bromo-2-deoxy-5-methyluridine-3,5-diacetate 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: 85.0%

O-2,2'-cyclo-5-methyluridine (22423-26-3) → 2'-bromothymidine (95585-76-5)

Guidance literature:

With pyridine; Pyridine hydrobromide; for 3h; Heating;

DOI:10.1039/c39940001255

Reference yield:

D-xylofuranose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) → 2'-bromothymidine (95585-76-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 77 percent / CuSO₄, H₂SO₄ / 18 h / Ambient temperature

2: 86 percent / 0.2percent HCl / 6 h / Ambient temperature

3: 91 percent / pyridine / 5 h

4: 1.) AcOH, Ac₂O, H₂SO₄, 2.) SnCl₄, 3.) MeONa

5: 55 percent / PhOCO₂Ph, NaHCO₃ / 4 h / 140 - 150 °C

6: 85 percent / pyridinium bromide, pyridine / 3 h / Heating

With pyridine; bis(phenyl) carbonate; hydrogenchloride; sulfuric acid; sodium methylate; Pyridine hydrobromide; acetic anhydride; tin(IV) chloride; sodium hydrogencarbonate; copper(II) sulfate; acetic acid;

DOI:10.1039/c39940001255

Reference yield:

3,5,6-tri-O-acetyl-1,2-O-isopropylidene-α-D-xylofuranose (42927-45-7) → 2'-bromothymidine (95585-76-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) AcOH, Ac₂O, H₂SO₄, 2.) SnCl₄, 3.) MeONa

2: 55 percent / PhOCO₂Ph, NaHCO₃ / 4 h / 140 - 150 °C

3: 85 percent / pyridinium bromide, pyridine / 3 h / Heating

With pyridine; bis(phenyl) carbonate; sulfuric acid; sodium methylate; Pyridine hydrobromide; acetic anhydride; tin(IV) chloride; sodium hydrogencarbonate; acetic acid;

DOI:10.1039/c39940001255

upstream raw materials:

O-2,2'-cyclo-5-methyluridine

D-xylofuranose

3,5,6-tri-O-acetyl-1,2-O-isopropylidene-α-D-xylofuranose

1,2-O-isopropylidene-α-D-xylose

Downstream raw materials:

thymidine

5'-O-trityl-2,3'-anhydrothymidine

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

3'-azido-2',3'-deoxythymidine