Toluene-4-sulfonic acid (2S,3S)-3-benzyloxy-6-oxo-3,6-dihydro-2H-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2S,3S)-3-benzyloxy-6-oxo-3,6-dihydro-2H-pyran-2-ylmethyl ester
• CAS No.: 116096-55-0
• Molecular Formula: C₂₀H₂₀O₆S
• Molecular Weight: 388.441
• Mol file: 116096-55-0.mol

Synonyms:Toluene-4-sulfonic acid (2S,3S)-3-benzyloxy-6-oxo-3,6-dihydro-2H-pyran-2-ylmethyl ester

Chemical Property of Toluene-4-sulfonic acid (2S,3S)-3-benzyloxy-6-oxo-3,6-dihydro-2H-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (2S,3S)-3-benzyloxy-6-oxo-3,6-dihydro-2H-pyran-2-ylmethyl ester

There total 7 articles about Toluene-4-sulfonic acid (2S,3S)-3-benzyloxy-6-oxo-3,6-dihydro-2H-pyran-2-ylmethyl ester 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: 84.0%

(5S,6S)-5-(benzyloxy)-6-(hydroxymethyl)-5,6-dihydro-2H-pyran-2-one (100906-41-0) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (2S,3S)-3-benzyloxy-6-oxo-3,6-dihydro-2H-pyran-2-ylmethyl ester (116096-55-0)

Guidance literature:

In pyridine; at 0 ℃; for 15h;

DOI:10.1016/S0040-4039(00)96881-3

Reference yield:

2-O-benzyl-3,4-O-isopropylidene-L-threitol (84379-53-3) → Toluene-4-sulfonic acid (2S,3S)-3-benzyloxy-6-oxo-3,6-dihydro-2H-pyran-2-ylmethyl ester (116096-55-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 71 percent / PCC/Al₂O₃, NaOAc / CH₂Cl₂

2: 71 percent / methanol / 1 h / 25 °C

3: 1.) LiOH ; 2.) TFA / 1.) THF/MeOH; 2.) H₂O

4: 84 percent / pyridine / 15 h / 0 °C

With aluminum oxide; lithium hydroxide; sodium acetate; pyridinium chlorochromate; trifluoroacetic acid; In pyridine; methanol; dichloromethane;

DOI:10.1016/S0040-4039(00)96881-3

Reference yield:

diethyl-2,3-O-benzylidene-D-tartrate (21154-16-5,35572-31-7,89015-57-6,141042-56-0) → Toluene-4-sulfonic acid (2S,3S)-3-benzyloxy-6-oxo-3,6-dihydro-2H-pyran-2-ylmethyl ester (116096-55-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 91 percent / LiAlH₄/AlCl₃ / diethyl ether; CH₂Cl₂ / -40 deg C to reflux

2: 94 percent / TSOH

3: 71 percent / PCC/Al₂O₃, NaOAc / CH₂Cl₂

4: 71 percent / methanol / 1 h / 25 °C

5: 1.) LiOH ; 2.) TFA / 1.) THF/MeOH; 2.) H₂O

6: 84 percent / pyridine / 15 h / 0 °C

With aluminum oxide; lithium hydroxide; lithium aluminium tetrahydride; aluminium trichloride; sodium acetate; toluene-4-sulfonic acid; pyridinium chlorochromate; trifluoroacetic acid; In pyridine; methanol; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(00)96881-3

upstream raw materials:

(5S,6S)-5-(benzyloxy)-6-(hydroxymethyl)-5,6-dihydro-2H-pyran-2-one

p-toluenesulfonyl chloride

2-O-benzyl-3,4-O-isopropylidene-L-threitol

diethyl-2,3-O-benzylidene-D-tartrate

Downstream raw materials:

Toluene-4-sulfonic acid (R)-6-oxo-5,6-dihydro-2H-pyran-2-ylmethyl ester

(+)-anamarine

Toluene-4-sulfonic acid (2R,6R)-6-isopropoxy-3,6-dihydro-2H-pyran-2-ylmethyl ester

((2R,6R)-6-Isopropoxy-3,6-dihydro-2H-pyran-2-ylmethyl)-triphenyl-phosphonium; iodide