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

Base Information

• Chemical Name: (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-(2-(((benzyloxy)carbonyl)amino)ethoxy) tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS No.: 127299-68-7
• Molecular Formula: C₂₄H₃₁NO₁₂
• Molecular Weight: 525.51
• Mol file: 127299-68-7.mol

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

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

There total 12 articles about (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-(2-(((benzyloxy)carbonyl)amino)ethoxy) 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: 74.0%

benzyl 2-hydroxyethylcarbamate (77987-49-6) + per-O-acetyl-α-D-mannopyranose (4163-65-9) → (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-(2-(((benzyloxy)carbonyl)amino)ethoxy) tetrahydro-2H-pyran-3,4,5-triyl triacetate (127299-68-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; for 12h; Reflux;

DOI:10.1002/chem.200900923

Reference yield: 62.5%

benzyl 2-hydroxyethylcarbamate (77987-49-6) + 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate (121238-27-5) → (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-(2-(((benzyloxy)carbonyl)amino)ethoxy) tetrahydro-2H-pyran-3,4,5-triyl triacetate (127299-68-7)

Guidance literature:

With boron trifluoride diethyl etherate; In tetrahydrofuran; at -30 - 20 ℃; Molecular sieve;

DOI:10.1039/b910976e

Reference yield: 57.0%

benzyl 2-hydroxyethylcarbamate (77987-49-6) + phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside (13992-16-0,23661-28-1,24404-53-3,28512-68-7,65236-85-3,86782-39-0,121524-01-4,121570-34-1,108032-93-5) → (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-(2-(((benzyloxy)carbonyl)amino)ethoxy) tetrahydro-2H-pyran-3,4,5-triyl triacetate (127299-68-7)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at 0 - 20 ℃; for 12h; Molecular sieve; Inert atmosphere;

DOI:10.1021/acs.jmedchem.7b01345

upstream raw materials:

benzyl 2-hydroxyethylcarbamate

per-O-acetyl-α-D-mannopyranose

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate

D-Mannose pentaacetate

Downstream raw materials:

2-(N-benzyloxycarbonyl)aminoethyl α-D-mannopyranoside