1-(2-deoxy-3-O-methanesulfonyl-5-O-triphenylmethyl-4-C-triphenylmethyloxymethyl-α-L-erythro-pentofuranosyl)thymine

Base Information

• Chemical Name: 1-(2-deoxy-3-O-methanesulfonyl-5-O-triphenylmethyl-4-C-triphenylmethyloxymethyl-α-L-erythro-pentofuranosyl)thymine
• CAS No.: 148704-69-2
• Molecular Formula: C₅₀H₄₆N₂O₈S
• Molecular Weight: 834.99
• Mol file: 148704-69-2.mol

Synonyms:1-(2-deoxy-3-O-methanesulfonyl-5-O-triphenylmethyl-4-C-triphenylmethyloxymethyl-α-L-erythro-pentofuranosyl)thymine

Chemical Property of 1-(2-deoxy-3-O-methanesulfonyl-5-O-triphenylmethyl-4-C-triphenylmethyloxymethyl-α-L-erythro-pentofuranosyl)thymine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(2-deoxy-3-O-methanesulfonyl-5-O-triphenylmethyl-4-C-triphenylmethyloxymethyl-α-L-erythro-pentofuranosyl)thymine

There total 11 articles about 1-(2-deoxy-3-O-methanesulfonyl-5-O-triphenylmethyl-4-C-triphenylmethyloxymethyl-α-L-erythro-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:

1,2-O-isopropylidene-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose (55797-64-3,55797-65-4) → 1-(2-deoxy-3-O-methanesulfonyl-5-O-triphenylmethyl-4-C-triphenylmethyloxymethyl-α-L-erythro-pentofuranosyl)thymine (148704-69-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 97 percent / pyridine / 5 h / Ambient temperature

2: 1.) sulfuric acid, 2.) SnCl₄ / 1.) AcOH, RT, overnight, 2.) CH₂Cl₂, RT, overnight

3: 95 percent / conc. HCl / dioxane / 144 h / 30 °C

4: 97 percent / pyridine / 4 h / Ambient temperature

5: 94 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / acetonitrile / Ambient temperature

6: 98 percent / HCl / dimethylformamide / 0.67 h / 100 °C

7: 89 percent / 2,2'-azobis(2-methylpropionitrile), Bu₃SnH / toluene / 0.67 h / 100 °C

8: MeONa / methanol / Ambient temperature

9: pyridine / 1 h / 100 °C

10: pyridine / 5 h / Ambient temperature

With pyridine; hydrogenchloride; 2,2'-azobis(isobutyronitrile); sulfuric acid; tri-n-butyl-tin hydride; sodium methylate; tin(IV) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,4-dioxane; methanol; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1135/cccc19930409

Reference yield:

1-(3,5-di-O-benzoyl-4-C-benzoyloxymethyl-2-deoxy-α-L-erythro-pentofuranosyl)thymine (148704-66-9) → 1-(2-deoxy-3-O-methanesulfonyl-5-O-triphenylmethyl-4-C-triphenylmethyloxymethyl-α-L-erythro-pentofuranosyl)thymine (148704-69-2)

Guidance literature:

Multi-step reaction with 3 steps

1: MeONa / methanol / Ambient temperature

2: pyridine / 1 h / 100 °C

3: pyridine / 5 h / Ambient temperature

With pyridine; sodium methylate; In methanol;

DOI:10.1135/cccc19930409

Reference yield:

3,5-di-O-benzoyl-4-C-benzoyloxymethyl-1,2-O-isopropylidene-β-L-arabinofuranose (148704-59-0) → 1-(2-deoxy-3-O-methanesulfonyl-5-O-triphenylmethyl-4-C-triphenylmethyloxymethyl-α-L-erythro-pentofuranosyl)thymine (148704-69-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) sulfuric acid, 2.) SnCl₄ / 1.) AcOH, RT, overnight, 2.) CH₂Cl₂, RT, overnight

2: 95 percent / conc. HCl / dioxane / 144 h / 30 °C

3: 97 percent / pyridine / 4 h / Ambient temperature

4: 94 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / acetonitrile / Ambient temperature

5: 98 percent / HCl / dimethylformamide / 0.67 h / 100 °C

6: 89 percent / 2,2'-azobis(2-methylpropionitrile), Bu₃SnH / toluene / 0.67 h / 100 °C

7: MeONa / methanol / Ambient temperature

8: pyridine / 1 h / 100 °C

9: pyridine / 5 h / Ambient temperature

With pyridine; hydrogenchloride; 2,2'-azobis(isobutyronitrile); sulfuric acid; tri-n-butyl-tin hydride; sodium methylate; tin(IV) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,4-dioxane; methanol; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1135/cccc19930409

upstream raw materials:

methanesulfonyl chloride

trityl chloride

1,2-O-isopropylidene-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose

1-(2-deoxy-4-C-hydroxymethyl-α-L-erythro-pentofuranosyl)thymine