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

Base Information

• Chemical Name: (2R,3R,4S,5R,6S)-2-((benzoyloxy)methyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
• CAS No.: 172847-85-7
• Molecular Formula: C₄₁H₃₄O₉S
• Molecular Weight: 702.782
• Mol file: 172847-85-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about (2R,3R,4S,5R,6S)-2-((benzoyloxy)methyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate 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: 92.0%

2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl o-isopropenylphenylacetate + para-thiocresol (106-45-6) → (2R,3R,4S,5R,6S)-2-((benzoyloxy)methyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate (172847-85-7)

Guidance literature:

2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl o-isopropenylphenylacetate; para-thiocresol; In dichloromethane; at 0 ℃; for 0.5h; Molecular sieve;

With bis(trifluoromethanesulfonyl)amide; In dichloromethane; at 0 - 20 ℃; Molecular sieve;

DOI:10.1002/ejoc.202101367

Reference yield: 90.0%

p-methylphenyl 1-thio-β-D-glucopyranoside (1152-39-2) + benzoyl chloride (98-88-4) → (2R,3R,4S,5R,6S)-2-((benzoyloxy)methyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate (172847-85-7)

Guidance literature:

With pyridine; dmap; for 15h; Ambient temperature;

Reference yield: 83.0%

2,3,4,6-tetra-O-benzoyl-D-glucopyranose (627466-64-2) + para-thiocresol (106-45-6) → (2R,3R,4S,5R,6S)-2-((benzoyloxy)methyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate (172847-85-7)

Guidance literature:

With iodine; aluminium; In dichloromethane; at 20 ℃; for 2h; diastereoselective reaction; Inert atmosphere; Green chemistry;

DOI:10.1002/jccs.201600828

upstream raw materials:

p-methylphenyl 1-thio-β-D-glucopyranoside

benzoyl chloride

2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl iodide

para-thiocresol

Downstream raw materials:

methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

C₃₅H₃₀O₁₀

methyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl)-α-D-glucopyranoside

1,5-anhydro-tetra-O-benzoyl-D-glucitol

Refernces

• 1、 Singh, Adesh Kumar,Tiwari, Varsha,Mishra, Kunj Bihari,Gupta, Surabhi,Kandasamy, Jeyakumar. "Urea–hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones". supporting information. p. 1139 - 1144. Retrieved 2017/06/20.
• 2、 Bruneau, Alexandre,Roche, Maxime,Hamze, Abdallah,Brion, Jean-Daniel,Alami, Mouad,Messaoudi, Samir. "Stereoretentive palladium-catalyzed arylation, alkenylation, and alkynylation of 1-thiosugars and thiols using aminobiphenyl palladacycle precatalyst at room temperature". . p. 8375 - 8379. Retrieved 2015/06/02.