methyl [(2R,3R,4S,5R)-3,4,5-tribenzyloxy-6-oxo-tetrahydropyran-2-yl]acetate

Base Information

• Chemical Name: methyl [(2R,3R,4S,5R)-3,4,5-tribenzyloxy-6-oxo-tetrahydropyran-2-yl]acetate
• CAS No.: 88567-51-5
• Molecular Formula: C₂₉H₃₀O₇
• Molecular Weight: 490.553
• Mol file: 88567-51-5.mol

Synonyms:methyl [(2R,3R,4S,5R)-3,4,5-tribenzyloxy-6-oxo-tetrahydropyran-2-yl]acetate

Chemical Property of methyl [(2R,3R,4S,5R)-3,4,5-tribenzyloxy-6-oxo-tetrahydropyran-2-yl]acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl [(2R,3R,4S,5R)-3,4,5-tribenzyloxy-6-oxo-tetrahydropyran-2-yl]acetate

There total 4 articles about methyl [(2R,3R,4S,5R)-3,4,5-tribenzyloxy-6-oxo-tetrahydropyran-2-yl]acetate 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%

6-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose (88567-49-1,88567-50-4,93361-01-4,101802-94-2,101802-97-5,127875-38-1) → methyl [(2R,3R,4S,5R)-3,4,5-tribenzyloxy-6-oxo-tetrahydropyran-2-yl]acetate (88567-51-5)

Guidance literature:

With acetic anhydride; dimethyl sulfoxide;

DOI:10.1055/s-2005-921912

Reference yield: 71.0%

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) + acetic anhydride (108-24-7) → methyl [(2R,3R,4S,5R)-3,4,5-tribenzyloxy-6-oxo-tetrahydropyran-2-yl]acetate (88567-51-5)

Guidance literature:

With sulfuric acid; acetic acid; In water; at -15 - -10 ℃; for 2.5h; Inert atmosphere;

Reference yield:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) → methyl [(2R,3R,4S,5R)-3,4,5-tribenzyloxy-6-oxo-tetrahydropyran-2-yl]acetate (88567-51-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydrogencarbonate; potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / dichloromethane; water / 0.33 h / 0 °C

2: acetic acid; sulfuric acid / water / 2.5 h / -15 - -10 °C / Inert atmosphere

With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sulfuric acid; sodium hydrogencarbonate; acetic acid; potassium bromide; In dichloromethane; water;

upstream raw materials:

6-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose

1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Downstream raw materials:

N-<3-(1,3-dithian-2-ylidene)propyl>-(3S,4S,5S,6RS)-3,4,5-tris(benzyloxy)-6-hydroxy-2-piperidinone

2,3,4-tri-O-benzyl-1-C-n-butyl-α-D-glucopyranose

6-O-acetyl-2,3,4-tri-O-benzyl-1-C-n-butyl-α-D-glucopyranose