6-O-p-tolylsulfonyl-3,4-di-O-acetyl-D-glucal

Base Information

• Chemical Name: 6-O-p-tolylsulfonyl-3,4-di-O-acetyl-D-glucal
• CAS No.: 18546-25-3
• Molecular Formula: C₁₇H₂₀O₈S
• Molecular Weight: 384.407
• Mol file: 18546-25-3.mol

Synonyms:6-O-p-tolylsulfonyl-3,4-di-O-acetyl-D-glucal

Chemical Property of 6-O-p-tolylsulfonyl-3,4-di-O-acetyl-D-glucal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-O-p-tolylsulfonyl-3,4-di-O-acetyl-D-glucal

There total 18 articles about 6-O-p-tolylsulfonyl-3,4-di-O-acetyl-D-glucal 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: 90.0%

2,3,4-tri-O-acetyl-6-O-(p-toluenesulfonyl)-α-D-glucopyranosyl bromide (55500-08-8) → 6-O-p-tolylsulfonyl-3,4-di-O-acetyl-D-glucal (18546-25-3)

Guidance literature:

With β‐cyclodextrin; zinc; In water; at 20 ℃; for 1h; Sonication;

DOI:10.1002/cjoc.201180263

Reference yield: 88.0%

3,4-di-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (82295-98-5) + p-toluenesulfonyl chloride (98-59-9) → 6-O-p-tolylsulfonyl-3,4-di-O-acetyl-D-glucal (18546-25-3)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 20h;

DOI:10.1016/S0040-4020(02)00578-1

Reference yield: 85.0%

Acetic acid (2R,3R,4S,5R)-4,5-diacetoxy-6-bromo-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester (59202-80-1) + Acetic acid (2R,3R,4S,5R)-3-acetoxy-6-bromo-5-(toluene-4-sulfonyloxy)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-4-yl ester (103725-99-1) → 6-O-p-tolylsulfonyl-3,4-di-O-acetyl-D-glucal (18546-25-3)

Guidance literature:

With copper; zinc; In water; acetic acid; at -5 - 0 ℃; for 3h;

DOI:10.1016/0008-6215(89)85126-2

upstream raw materials:

D-glucose

6-O-p-toluenesulfonyl-D-arabino-hex-1-enitol

acetic anhydride

Acetic acid (2R,3R,4S,5R)-4,5-diacetoxy-6-bromo-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

Downstream raw materials:

(+)-(5S,6R)-5-Acetoxy-5,6-dihydro-6-(tosyloxymethyl)-2H-pyran-2-one

3,4-Di-O-acetyl-2-deoxy-2-iodo-6-O-p-toluenesulphonyl-α-D-mannopyranose

1,3,4-Tri-O-acetyl-2-deoxy-2-iodo-6-O-p-toluenesulphonyl-α-D-mannopyranose

acetyl 2-deoxy-3,4-di-O-acetyl-6-O-tosyl-α/β-D-glucopyranose

Refernces

• 1、 Vadhadiya, Paresh M.,Jean, Marc-Alexandre,Bouzriba, Chahrazed,Tremblay, Thomas,Lagüe, Patrick,Fortin, Sébastien,Boukouvalas, John,Giguère, Denis. "Diversity-Oriented Synthesis of Diol-Based Peptidomimetics as Potential HIV Protease Inhibitors and Antitumor Agents". . p. 1779 - 1791. Retrieved 2018.
• 2、 Kandasamy, Jeyakumar,Singh, Adesh Kumar,Venkatesh, Rapelly. "Palladium-Catalyzed One-Pot Stereospecific Synthesis of 2-Deoxy Aryl C-Glycosides from Glycals and Anilines in the Presence of tert-Butyl Nitrite". . p. 4215 - 4230. Retrieved 2019/11/14.
• 3、 Mizia, J. Colin,Bennett, Clay S.. "Reagent Controlled Direct Dehydrative Glycosylation with 2-Deoxy Sugars: Construction of the Saquayamycin Z Pentasaccharide". . p. 5922 - 5927. Retrieved 2019/08/27.