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

Base Information

• Chemical Name: (2S,3S,4R,5R,6S)-2-methyl-6-(p-tolylthio)tetrahydro-2H-pyranol
• CAS No.: 628308-75-8
• Molecular Formula: C₁₃H₁₈O₄S
• Molecular Weight: 270.35
• Mol file: 628308-75-8.mol

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

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

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (2S,3S,4R,5R,6S)-2-methyl-6-(p-tolylthio)tetrahydro-2H-pyranol 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%

p-tolyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside (620951-70-4) → (2S,3S,4R,5R,6S)-2-methyl-6-(p-tolylthio)tetrahydro-2H-pyranol (628308-75-8)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 0.333333h;

DOI:10.1055/s-2007-965995

Reference yield:

L-rhamnose (73-34-7) → (2S,3S,4R,5R,6S)-2-methyl-6-(p-tolylthio)tetrahydro-2H-pyranol (628308-75-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / DMAP / pyridine / 0.5 h / 20 °C

2: 81 percent / BF₃*OEt₂ / CH₂Cl₂ / 0 - 20 °C

3: 99 percent / NaOMe / methanol / 0.33 h / 20 °C

With dmap; boron trifluoride diethyl etherate; sodium methylate; In pyridine; methanol; dichloromethane;

DOI:10.1055/s-2007-965995

Reference yield:

1,2,3,4-tetra-O-acetyl-L-rhamnopyranose (7404-35-5,17081-04-8,20853-37-6,24332-95-4,27821-10-9,27821-11-0,33947-15-8,34371-40-9,34371-41-0,35521-79-0,36807-81-5,36807-82-6,50615-78-6,51921-33-6,62182-03-0,64913-16-2,70004-81-8,84622-47-9,87303-56-8,108942-32-1,108942-33-2,109430-94-6,143394-72-3,30021-94-4) → (2S,3S,4R,5R,6S)-2-methyl-6-(p-tolylthio)tetrahydro-2H-pyranol (628308-75-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / BF₃*OEt₂ / CH₂Cl₂ / 0 - 20 °C

2: 99 percent / NaOMe / methanol / 0.33 h / 20 °C

With boron trifluoride diethyl etherate; sodium methylate; In methanol; dichloromethane;

DOI:10.1055/s-2007-965995

upstream raw materials:

p-tolyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside

L-rhamnose

1,2,3,4-tetra-O-acetyl-L-rhamnopyranose

L-rhamnose

Downstream raw materials:

p-tolyl 4-O-acetyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

(2'S,3'S)-para-tolyl 3,4-O-(2',3'-dimethoxybutan-2',3'-diyl)-1-thio-α-L-rhamnopyranoside

p–tolyl 2,3-O-isopropylidene-1-thio-α-L-rhammopyranoside

p-tolyl 2,4-di-O-acetyl-1-thio-α-L-rhamnopyranoside