1-(3'-Azido-2',3'-dideoxy-5'-O-triphenylmethyl-α-L-threo-pentofuranosyl)thymine

Base Information

• Chemical Name: 1-(3'-Azido-2',3'-dideoxy-5'-O-triphenylmethyl-α-L-threo-pentofuranosyl)thymine
• CAS No.: 137147-02-5
• Molecular Formula: C₂₉H₂₇N₅O₄
• Molecular Weight: 509.564
• Mol file: 137147-02-5.mol

Synonyms:1-(3'-Azido-2',3'-dideoxy-5'-O-triphenylmethyl-α-L-threo-pentofuranosyl)thymine

Chemical Property of 1-(3'-Azido-2',3'-dideoxy-5'-O-triphenylmethyl-α-L-threo-pentofuranosyl)thymine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(3'-Azido-2',3'-dideoxy-5'-O-triphenylmethyl-α-L-threo-pentofuranosyl)thymine

There total 12 articles about 1-(3'-Azido-2',3'-dideoxy-5'-O-triphenylmethyl-α-L-threo-pentofuranosyl)thymine 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: 80.0%

3'-O-Methylsulfonyl-5'-O-triphenylmethyl-α-L-thymidine (137147-01-4) → 1-(3'-Azido-2',3'-dideoxy-5'-O-triphenylmethyl-α-L-threo-pentofuranosyl)thymine (137147-02-5)

Guidance literature:

With lithium azide; In N,N-dimethyl-formamide; for 3h; Heating;

DOI:10.1055/s-1991-26543

Reference yield:

1-<2',3',5'-Tri-O-benzoyl-α-L-arabinofuranosyl>thymine (20290-92-0) → 1-(3'-Azido-2',3'-dideoxy-5'-O-triphenylmethyl-α-L-threo-pentofuranosyl)thymine (137147-02-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 80 percent / NaOMe / methanol / 1 h / Ambient temperature

2: 100 percent / pyridine / 5 h / Ambient temperature

3: 68 percent / 4-(dimethylamino)pyridine / acetonitrile / 16 h / Ambient temperature

4: 83 percent / AIBN, Bu₃SnH / toluene / 3 h / 75 °C

5: 41 percent / Bu₄NF / tetrahydrofuran / 0.5 h / Ambient temperature

6: pyridine / 3 h / Heating

7: 180 mg / pyridine / 96 h / -10 °C

8: 80 percent / LiN₃ / dimethylformamide / 3 h / Heating

With pyridine; dmap; lithium azide; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium methylate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1055/s-1991-26543

Reference yield:

L-(+)-arabinose (87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2) → 1-(3'-Azido-2',3'-dideoxy-5'-O-triphenylmethyl-α-L-threo-pentofuranosyl)thymine (137147-02-5)

Guidance literature:

Multi-step reaction with 12 steps

1: H₂SO₄, CaSO₄

2: pyridine / 1 h / 50 °C

3: 95 percent / H₂SO₄ conc. / acetic acid / 4 h / Ambient temperature

4: 60 percent / Me₃SiNHSiMe₃, Me₃SiCl, SnCl₄ / acetonitrile / 1 h / Heating

5: 80 percent / NaOMe / methanol / 1 h / Ambient temperature

6: 100 percent / pyridine / 5 h / Ambient temperature

7: 68 percent / 4-(dimethylamino)pyridine / acetonitrile / 16 h / Ambient temperature

8: 83 percent / AIBN, Bu₃SnH / toluene / 3 h / 75 °C

9: 41 percent / Bu₄NF / tetrahydrofuran / 0.5 h / Ambient temperature

10: pyridine / 3 h / Heating

11: 180 mg / pyridine / 96 h / -10 °C

12: 80 percent / LiN₃ / dimethylformamide / 3 h / Heating

With pyridine; dmap; calcium sulfate; chloro-trimethyl-silane; lithium azide; 2,2'-azobis(isobutyronitrile); sulfuric acid; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium methylate; tin(IV) chloride; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; acetic acid; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1055/s-1991-26543

upstream raw materials:

3'-O-Methylsulfonyl-5'-O-triphenylmethyl-α-L-thymidine

1-<2',3',5'-Tri-O-benzoyl-α-L-arabinofuranosyl>thymine

L-(+)-arabinose

1-[(2R,4R,5S)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methylpyrimidine-2,4-dione

Downstream raw materials:

1-(3'-Azido-2',3'-dideoxy-α-L-threo-pentofuranosyl)thymine