2,3,5-tri-O-p-methoxybenzyl-1,4-dideoxy-1,4-[[(2S,3S,4R,5R)-4,6-O-benzylidene-2,5-di-O-p-methoxybenzyl-3-(sulfooxy)hexyl]-(R)-epi-sulfoniumylidene]-D-arabinitol inner salt

Base Information

• Chemical Name: 2,3,5-tri-O-p-methoxybenzyl-1,4-dideoxy-1,4-[[(2S,3S,4R,5R)-4,6-O-benzylidene-2,5-di-O-p-methoxybenzyl-3-(sulfooxy)hexyl]-(R)-epi-sulfoniumylidene]-D-arabinitol inner salt
• CAS No.: 922164-05-4
• Molecular Formula: C₅₈H₆₆O₁₆S₂
• Molecular Weight: 1083.28
• Mol file: 922164-05-4.mol

Synonyms:2,3,5-tri-O-p-methoxybenzyl-1,4-dideoxy-1,4-[[(2S,3S,4R,5R)-4,6-O-benzylidene-2,5-di-O-p-methoxybenzyl-3-(sulfooxy)hexyl]-(R)-epi-sulfoniumylidene]-D-arabinitol inner salt

Chemical Property of 2,3,5-tri-O-p-methoxybenzyl-1,4-dideoxy-1,4-[[(2S,3S,4R,5R)-4,6-O-benzylidene-2,5-di-O-p-methoxybenzyl-3-(sulfooxy)hexyl]-(R)-epi-sulfoniumylidene]-D-arabinitol inner salt

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,5-tri-O-p-methoxybenzyl-1,4-dideoxy-1,4-[[(2S,3S,4R,5R)-4,6-O-benzylidene-2,5-di-O-p-methoxybenzyl-3-(sulfooxy)hexyl]-(R)-epi-sulfoniumylidene]-D-arabinitol inner salt

There total 4 articles about 2,3,5-tri-O-p-methoxybenzyl-1,4-dideoxy-1,4-[[(2S,3S,4R,5R)-4,6-O-benzylidene-2,5-di-O-p-methoxybenzyl-3-(sulfooxy)hexyl]-(R)-epi-sulfoniumylidene]-D-arabinitol inner salt 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: 77.0%

4,6-O-benzylidene-2,5-di-O-p-methoxybenzyl-D-mannitol 1,3-cyclic sulfate (913534-62-0) + (2R,3S,4S)-3,4-bis((4-methoxybenzyl)oxy)-2-(((4-methoxybenzyl)oxy)methyl)tetrahydrothiophene (635316-05-1) → 2,3,5-tri-O-p-methoxybenzyl-1,4-dideoxy-1,4-[[(2S,3S,4R,5R)-4,6-O-benzylidene-2,5-di-O-p-methoxybenzyl-3-(sulfooxy)hexyl]-(R)-epi-sulfoniumylidene]-D-arabinitol inner salt (922164-05-4)

Guidance literature:

With potassium carbonate; In various solvent(s); at 65 - 70 ℃; for 42h;

DOI:10.1021/jo061944v

Reference yield:

4,6-O-benzylidene-2,5-di-O-p-methoxybenzyl-D-mannitol (913534-64-2) → 2,3,5-tri-O-p-methoxybenzyl-1,4-dideoxy-1,4-[[(2S,3S,4R,5R)-4,6-O-benzylidene-2,5-di-O-p-methoxybenzyl-3-(sulfooxy)hexyl]-(R)-epi-sulfoniumylidene]-D-arabinitol inner salt (922164-05-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / triethylamine; thionyl chloride / CH₂Cl₂ / 0.5 h / cooling

2: 86 percent / sodium periodate; RuCl₃ / acetonitrile; CCl₄; H₂O / 2 h / 20 °C

3: 77 percent / anhydrous K₂CO₃ / various solvent(s) / 42 h / 65 - 70 °C

With ruthenium trichloride; sodium periodate; thionyl chloride; potassium carbonate; triethylamine; In tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1021/jo061944v

Reference yield:

1,3:4,6-di-O-benzylidene-2,5-bis-O-(p-methoxybenzyl)-D-mannitol → 2,3,5-tri-O-p-methoxybenzyl-1,4-dideoxy-1,4-[[(2S,3S,4R,5R)-4,6-O-benzylidene-2,5-di-O-p-methoxybenzyl-3-(sulfooxy)hexyl]-(R)-epi-sulfoniumylidene]-D-arabinitol inner salt (922164-05-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 73 percent / p-toluenesulfonic acid / methanol / 4 h / 20 °C

2: 76 percent / triethylamine; thionyl chloride / CH₂Cl₂ / 0.5 h / cooling

3: 86 percent / sodium periodate; RuCl₃ / acetonitrile; CCl₄; H₂O / 2 h / 20 °C

4: 77 percent / anhydrous K₂CO₃ / various solvent(s) / 42 h / 65 - 70 °C

With ruthenium trichloride; sodium periodate; thionyl chloride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; In methanol; tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1021/jo061944v

upstream raw materials:

4,6-O-benzylidene-2,5-di-O-p-methoxybenzyl-D-mannitol 1,3-cyclic sulfate

(2R,3S,4S)-3,4-bis((4-methoxybenzyl)oxy)-2-(((4-methoxybenzyl)oxy)methyl)tetrahydrothiophene

4,6-O-benzylidene-2,5-di-O-p-methoxybenzyl-D-mannitol

4,6-O-benzylidene-2,5-di-O-p-methoxybenzyl-D-mannitol 1,3-cyclic sulfite