(2S,4R)-4-(p-tolylsulfonyloxy)-2-[(1R)-1,2-cyclohexylidenedioxyethyl]tetrahydrofuran

Base Information

• Chemical Name: (2S,4R)-4-(p-tolylsulfonyloxy)-2-[(1R)-1,2-cyclohexylidenedioxyethyl]tetrahydrofuran
• CAS No.: 439114-55-3
• Molecular Formula: C₁₉H₂₆O₆S
• Molecular Weight: 382.478
• Mol file: 439114-55-3.mol

Synonyms:(2S,4R)-4-(p-tolylsulfonyloxy)-2-[(1R)-1,2-cyclohexylidenedioxyethyl]tetrahydrofuran

Chemical Property of (2S,4R)-4-(p-tolylsulfonyloxy)-2-[(1R)-1,2-cyclohexylidenedioxyethyl]tetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-4-(p-tolylsulfonyloxy)-2-[(1R)-1,2-cyclohexylidenedioxyethyl]tetrahydrofuran

There total 2 articles about (2S,4R)-4-(p-tolylsulfonyloxy)-2-[(1R)-1,2-cyclohexylidenedioxyethyl]tetrahydrofuran 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: 79.5%

5,6-O-cyclohexylidene-4-O-(tert-butyldimethylsilyl)-1,2-di-O-tosyl-3-deoxy-D-ribo-hexitol → (2S,4R)-4-(p-tolylsulfonyloxy)-2-[(1R)-1,2-cyclohexylidenedioxyethyl]tetrahydrofuran (439114-55-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1039/b109785g

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → (2S,4R)-4-(p-tolylsulfonyloxy)-2-[(1R)-1,2-cyclohexylidenedioxyethyl]tetrahydrofuran (439114-55-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 88.3 percent / DMAP / pyridine / 0 - 20 °C

2: 79.5 percent / TBAF / tetrahydrofuran / 20 °C

With dmap; tetrabutyl ammonium fluoride; In tetrahydrofuran; pyridine;

DOI:10.1039/b109785g

Reference yield:

(2S,4R)-4-(p-tolylsulfonyloxy)-2-[(1R)-1,2-cyclohexylidenedioxyethyl]tetrahydrofuran (439114-55-3) → 9-{(3S,5S)-5-[(1R)-1,2-dihydroxyethyl]tetrahydrofuran-3-yl}-N6-benzoyladenine (439114-58-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 62.6 percent / K₂CO₃; 18-crown-6 / dimethylformamide / 15 h / 75 - 80 °C

2: TMSCl / pyridine

3: 290 mg / aq. CF₃COOH / CH₂Cl₂ / 0 °C

With chloro-trimethyl-silane; 18-crown-6 ether; potassium carbonate; trifluoroacetic acid; In pyridine; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b109785g

upstream raw materials:

p-toluenesulfonyl chloride

Downstream raw materials:

9-{(3S,5S)-5-[(1R)-1,2-dihydroxyethyl]tetrahydrofuran-3-yl}-N⁶-benzoyladenine

N-{9-[5-(1,4-dioxa-spiro[4.5]dec-2-yl)-tetrahydro-furan-3-yl]-9H-purin-6-yl}-benzamide