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

Base Information

• Chemical Name: 1-(3-O-benzyl-2,5-di-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-erythro-pentofuranosyl)thymine
• CAS No.: 293751-07-2
• Molecular Formula: C₂₁H₂₈N₂O₁₃S₃
• Molecular Weight: 612.657
• Mol file: 293751-07-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

methanesulfonyl chloride (124-63-0) + 1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-erythro-pentofuranosyl)thymine (293751-06-1) → 1-(3-O-benzyl-2,5-di-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-erythro-pentofuranosyl)thymine (293751-07-2)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 5h;

DOI:10.1021/jo000232g

Reference yield: 93.0%

methanesulfonyl chloride (124-63-0) + 1-(3-O-benzyl-4-C-hydroxymethyl-β-D-erythro-pentofuranosyl)thymine (552856-37-8) → 1-(3-O-benzyl-2,5-di-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-erythro-pentofuranosyl)thymine (293751-07-2)

Guidance literature:

With pyridine; at 0 - 15 ℃; for 3h;

DOI:10.1039/b208864a

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-2,5-di-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-erythro-pentofuranosyl)thymine (293751-07-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / NH₃ / methanol

2: 93 percent / pyridine

With pyridine; ammonia; In methanol;

DOI:10.1081/NCN-120022818

upstream raw materials:

methanesulfonyl chloride

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

1-(3-O-benzyl-4-C-hydroxymethyl-β-D-erythro-pentofuranosyl)thymine

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

Downstream raw materials:

(1S,3R,4S,7S)-7-benzyloxy-1-(methanesulfonyloxymethyl)-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

(1S,3R,4S,7S)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

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

(1R,3R,4R,7S)-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-5-methyl-3-(4-benzoyl-5-methylcytosin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane