O¹,O²-isopropylidene-O³-(toluene-4-sulfonyl)-5-deoxy-α-D-xylofuranose

Base Information

• Chemical Name: O¹,O²-isopropylidene-O³-(toluene-4-sulfonyl)-5-deoxy-α-D-xylofuranose
• CAS No.: 16713-89-6
• Molecular Formula: C₁₅H₂₀O₆S
• Molecular Weight: 328.386
• Mol file: 16713-89-6.mol

Synonyms:O¹,O²-isopropylidene-O³-(toluene-4-sulfonyl)-5-deoxy-α-D-xylofuranose

Chemical Property of O¹,O²-isopropylidene-O³-(toluene-4-sulfonyl)-5-deoxy-α-D-xylofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O¹,O²-isopropylidene-O³-(toluene-4-sulfonyl)-5-deoxy-α-D-xylofuranose

There total 5 articles about O¹,O²-isopropylidene-O³-(toluene-4-sulfonyl)-5-deoxy-α-D-xylofuranose 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%

5-deoxy-5-iodo-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-α-D-xylofuranose (29873-56-1) → O1,O2-isopropylidene-O3-(toluene-4-sulfonyl)-5-deoxy-α-D-xylofuranose (16713-89-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 25 ℃;

DOI:10.1016/0008-6215(84)85225-8

Reference yield:

1,2-O-isopropylidene-3-O-tosyl-α-D-xylopentofuranose (16713-88-5) → O1,O2-isopropylidene-O3-(toluene-4-sulfonyl)-5-deoxy-α-D-xylofuranose (16713-89-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / I₂, triphenylphosphine, imidazole / toluene / 0.33 h / Ambient temperature

2: 46 percent / zinc/silver-graphite / tetrahydrofuran / 12 h / 60 °C

With 1H-imidazole; silver-graphite; iodine; triphenylphosphine; zinc; In tetrahydrofuran; toluene;

DOI:10.1021/jo00006a047

Reference yield:

p-toluenesulfonyl chloride (98-59-9) + 1,2-O-isopropylidene-5-methyl-5-deoxy-α-D-xylofuranose (4152-79-8,33156-02-4,37105-87-6,37105-91-2,37105-93-4,53597-97-0,97059-40-0) → O1,O2-isopropylidene-O3-(toluene-4-sulfonyl)-5-deoxy-α-D-xylofuranose (16713-89-6)

Guidance literature:

With pyridine;

upstream raw materials:

p-toluenesulfonyl chloride

1,2-O-isopropylidene-5-methyl-5-deoxy-α-D-xylofuranose

5-deoxy-5-iodo-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-α-D-xylofuranose

1,2-O-isopropylidene-3-O-tosyl-α-D-xylopentofuranose

Downstream raw materials:

1,2-di-O-acetyl-5-deoxy-3-O-p-tolylsulfonyl-D-xylofuranose

methyl 5-deoxy-3-O-(p-toluenesulfonyl)-β-D-xylofuranoside

methyl 5-deoxy-3-O-(p-toluenesulfonyl)-α-D-xylofuranoside

methyl-2,5-didesoxy-2-C-methyl-3-O-benzyl-α-D-arabinofuranoside