(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Base Information

• Chemical Name: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS No.: 71692-91-6
• Molecular Formula: C₄₂H₅₀O₁₅
• Molecular Weight: 794.85
• Mol file: 71692-91-6.mol

Synonyms:(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property of (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

There total 41 articles about (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)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: 98.0%

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) + C24H32O11S → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (71692-91-6)

Guidance literature:

With trifluoromethylsulfonic anhydride; In dichloromethane; at 0 ℃; for 0.5h; Molecular sieve;

DOI:10.1021/jacs.6b08305

Reference yield: 97.0%

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) + ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (32934-24-0,41670-79-5,52645-73-5,55722-49-1,79389-52-9,99031-86-4,125354-48-5,126187-25-5) → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (71692-91-6)

Guidance literature:

With silver trifluoromethanesulfonate; dimethylbromosulphonium bromide; In dichloromethane; at -35 - 20 ℃; Inert atmosphere; Darkness; Molecular sieve;

DOI:10.1002/adsc.200800190

Reference yield: 96.0%

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) + 2-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]pyridine (17430-62-5) → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (71692-91-6)

Guidance literature:

With trifluoromethylsulfonic anhydride; In dichloromethane; at -72 - 20 ℃; for 0.416667h; Reagent/catalyst; Concentration; Inert atmosphere; Molecular sieve;

DOI:10.1016/j.tetlet.2014.11.066

upstream raw materials:

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

Pent-4-enyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

methyl 2,3,6-tri-O-benzyl-4-O-trimethylsilyl-α-D-glucopyranoside

2-(acetoxymethyl)-6-fluorotetrahydro-2H-pyran-3,4,5-triyl triacetate

Downstream raw materials:

3,4-epoxybutyl β-cellobioside

methyl (sodium β-D-glucopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

C₃₆H₄₁O₁₁^(1-)*Na⁽¹⁺⁾

methyl (sodium 2,3,4-tri-O-methyl-β-D-glucopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside