(2S,3R,4R,5S,6R)-2-methyl-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Base Information

• Chemical Name: (2S,3R,4R,5S,6R)-2-methyl-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS No.: 153658-86-7
• Molecular Formula: C₁₉H₂₄O₇S
• Molecular Weight: 396.461
• Mol file: 153658-86-7.mol

Synonyms:(2S,3R,4R,5S,6R)-2-methyl-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property of (2S,3R,4R,5S,6R)-2-methyl-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5S,6R)-2-methyl-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

There total 7 articles about (2S,3R,4R,5S,6R)-2-methyl-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 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: 95.0%

1,2,3,4-tetra-O-acetyl-L-fucopyranose (7404-35-5,17081-04-8,20853-37-6,27821-10-9,27821-11-0,30021-94-4,33947-15-8,34371-40-9,34371-41-0,35521-79-0,36807-81-5,36807-82-6,50615-78-6,51921-33-6,62182-03-0,64913-16-2,70004-81-8,84622-47-9,87303-56-8,108942-32-1,108942-33-2,109430-94-6,143394-72-3,24332-95-4) + para-thiocresol (106-45-6) → (2S,3R,4R,5S,6R)-2-methyl-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (153658-86-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1039/c9ob00057g

Reference yield: 95.0%

6-deoxy-L-galactose (73-34-7,87-96-7,488-79-9,551-63-3,609-01-8,643-17-4,643-18-5,4164-09-4,6014-42-2,6155-36-8,6189-71-5,6696-41-9,6736-43-2,13224-93-6,22611-09-2,28161-49-1,28161-50-4,28161-52-6,45864-36-6,63814-64-2,71116-59-1,71116-61-5,72598-05-1,87936-88-7,87936-89-8,97466-79-0,116908-82-8,120442-60-6,123484-22-0,133576-32-6) + acetic anhydride (108-24-7) + para-thiocresol (106-45-6) → (2S,3R,4R,5S,6R)-2-methyl-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (153658-86-7)

Guidance literature:

6-deoxy-L-galactose; acetic anhydride; With pyridine; at 20 ℃; for 8h;

para-thiocresol; With boron trifluoride diethyl etherate; In dichloromethane; Cooling with ice;

Reference yield: 67.0%

Acetic acid (3S,4R,5R,6S)-4,5-diacetoxy-2-(bis-benzyloxy-phosphanyloxy)-6-methyl-tetrahydro-pyran-3-yl ester (149717-37-3) + para-thiocresol (106-45-6) → (2S,3R,4R,5S,6R)-2-methyl-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (153658-86-7)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1021/jo00083a032

upstream raw materials:

Acetic acid (3S,4R,5R,6S)-4,5-diacetoxy-2-(bis-benzyloxy-phosphanyloxy)-6-methyl-tetrahydro-pyran-3-yl ester

para-thiocresol

6-deoxy-L-galactose

acetic anhydride

Downstream raw materials:

p-methylphenyl 1-thio-β-L-fucopyranoside

p-methylphenyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside

p-methylphenyl 2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-6-O-tert-butyldiphenylsilyl-4-O-levulinyl-1-thio-β-D-galactopyranoside

p-methylphenyl 2-O-benzoyl-4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-6-O-tert-butyldiphenylsilyl-3-O-p-methoxybenzyl-1-thio-β-D-galactopyranoside