1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-2-O-trifluoromethanesulfonyl-β-D-threo-pentofuranosyl)-thymine

Base Information

• Chemical Name: 1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-2-O-trifluoromethanesulfonyl-β-D-threo-pentofuranosyl)-thymine
• CAS No.: 552856-40-3
• Molecular Formula: C₂₁H₂₅F₃N₂O₁₃S₃
• Molecular Weight: 666.628
• Mol file: 552856-40-3.mol

Synonyms:1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-2-O-trifluoromethanesulfonyl-β-D-threo-pentofuranosyl)-thymine

Chemical Property of 1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-2-O-trifluoromethanesulfonyl-β-D-threo-pentofuranosyl)-thymine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-2-O-trifluoromethanesulfonyl-β-D-threo-pentofuranosyl)-thymine

There total 11 articles about 1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-2-O-trifluoromethanesulfonyl-β-D-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: 97.0%

trifluoromethylsulfonic anhydride (358-23-6) + 1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-threo-pentofuranosyl)thymine (552856-39-0) → 1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-2-O-trifluoromethanesulfonyl-β-D-threo-pentofuranosyl)-thymine (552856-40-3)

Guidance literature:

With pyridine; dmap; In dichloromethane; at -70 - 0 ℃; for 4h; Inert atmosphere;

DOI:10.1021/jo302036h

Reference yield:

1-(2-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxymethyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl)thymine (293751-04-9) → 1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-2-O-trifluoromethanesulfonyl-β-D-threo-pentofuranosyl)-thymine (552856-40-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / NH₃ / methanol

2: 93 percent / pyridine

3: 91 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile

4: 98 percent / sulfuric acid / H₂O; acetone / Heating

5: 80 percent / 4-(dimethylamino)pyridine; pyridine / CH₂Cl₂ / 0 °C

With pyridine; dmap; sulfuric acid; ammonia; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; water; acetone; acetonitrile;

DOI:10.1081/NCN-120022818

Reference yield:

1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-erythro-pentofuranosyl)thymine (293751-06-1) → 1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-2-O-trifluoromethanesulfonyl-β-D-threo-pentofuranosyl)-thymine (552856-40-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / pyridine

2: 91 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile

3: 98 percent / sulfuric acid / H₂O; acetone / Heating

4: 80 percent / 4-(dimethylamino)pyridine; pyridine / CH₂Cl₂ / 0 °C

With pyridine; dmap; sulfuric acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; water; acetone; acetonitrile;

DOI:10.1081/NCN-120022818

upstream raw materials:

trifluoromethylsulfonic anhydride

1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-threo-pentofuranosyl)thymine

1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-erythro-pentofuranosyl)thymine

1-(3-O-benzyl-2,5-di-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-erythro-pentofuranosyl)thymine

Downstream raw materials:

(1R,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-5-trifluoroacetyl-2-oxa-5-azabicyclo[2.2.1]heptane

(1R,3R,4R,7S)-7-benzyloxy-1-(4,4'-dimethoxytrityl)oxymethyl-3-(thymin-1-yl)-5-trifluoroacetyl-2-oxa-5-azabicyclo[2.2.1]heptane

(1R,3R,4R,7S)-7-benzyloxy-1-(4,4'-dimethoxytrityl)oxymethyl-3-(5-methylcytosin-1-yl)-5-trifluoroacetyl-2-oxa-5-azabicyclo[2.2.1]heptane

Acetic acid (1R,3R,4R,7S)-1-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-methyl-3-(5-methyl-2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-2-oxa-5-aza-bicyclo[2.2.1]hept-7-yl ester