(2R,3R,4S,5S,6S)-2-(acetoxymethyl)-6-(2-(benzyloxy)-2-oxoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Base Information

• Chemical Name: (2R,3R,4S,5S,6S)-2-(acetoxymethyl)-6-(2-(benzyloxy)-2-oxoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS No.: 1118624-81-9
• Molecular Formula: C₂₃H₂₈O₁₂
• Molecular Weight: 496.468
• Mol file: 1118624-81-9.mol

Synonyms:(2R,3R,4S,5S,6S)-2-(acetoxymethyl)-6-(2-(benzyloxy)-2-oxoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property of (2R,3R,4S,5S,6S)-2-(acetoxymethyl)-6-(2-(benzyloxy)-2-oxoethoxy)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,5S,6S)-2-(acetoxymethyl)-6-(2-(benzyloxy)-2-oxoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

There total 4 articles about (2R,3R,4S,5S,6S)-2-(acetoxymethyl)-6-(2-(benzyloxy)-2-oxoethoxy)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: 68.0%

penta-O-acetyl-D-mannose (66888-27-5) + benzyl glycolate (30379-58-9) → (2R,3R,4S,5S,6S)-2-(acetoxymethyl)-6-(2-(benzyloxy)-2-oxoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1118624-81-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 21 ℃; for 16h; Inert atmosphere;

Reference yield: 68.0%

D-Mannose pentaacetate (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5) + benzyl glycolate (30379-58-9) → (2R,3R,4S,5S,6S)-2-(acetoxymethyl)-6-(2-(benzyloxy)-2-oxoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1118624-81-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 21 ℃; for 16h; Inert atmosphere;

DOI:10.1039/c5cc09518b

Reference yield: 55.0%

benzyl glycolate (30379-58-9) + acetic anhydride (108-24-7) + per-O-acetyl-α-D-mannopyranose (4163-65-9) → (2R,3R,4S,5S,6S)-2-(acetoxymethyl)-6-(2-(benzyloxy)-2-oxoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1118624-81-9)

Guidance literature:

benzyl glycolate; per-O-acetyl-α-D-mannopyranose; With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; for 73h; Inert atmosphere;

acetic anhydride; With pyridine; at 20 ℃;

DOI:10.1016/j.tet.2009.02.018

upstream raw materials:

benzyl glycolate

acetic anhydride

per-O-acetyl-α-D-mannopyranose

acetobromomannose