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

Base Information

• Chemical Name: (1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonoxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane
• CAS No.: 293751-05-0
• Molecular Formula: C₁₉H₂₂N₂O₈S
• Molecular Weight: 438.458
• Mol file: 293751-05-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 15 articles about (1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonoxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 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: 99.0%

methanesulfonyl chloride (124-63-0) + (1S,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (212970-84-8) → (1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonoxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (293751-05-0)

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1039/b307290h

Reference yield: 98.0%

1-(2-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxymethyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl)thymine (293751-04-9) → (1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonoxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (293751-05-0)

Guidance literature:

With sodium hydroxide; In dichloromethane; acetonitrile; at 25 ℃; Large scale;

Reference yield:

1,2-di-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxymethyl-5-O-methanesulfonyl-D-erythro-pentofuranose (293751-03-8) → (1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonoxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (293751-05-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 1 h / Heating

1.2: 88 percent / trimethylsilyl triflate / acetonitrile / 4 h / Heating

2.1: 94 percent / aq. NaOH / dioxane; H₂O / 1 h / 20 °C

With sodium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; In 1,4-dioxane; water; acetonitrile;

DOI:10.1021/jo010732p

upstream raw materials:

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

methanesulfonyl chloride

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

Acetic acid (3R,4S,5S)-2-acetoxy-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester

Downstream raw materials:

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

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

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