menthyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranoside

Base Information

• Chemical Name: menthyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranoside
• CAS No.: 1258282-08-4
• Molecular Formula: C₂₂H₃₅IO₈
• Molecular Weight: 554.42
• Mol file: 1258282-08-4.mol

Synonyms:menthyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranoside

Chemical Property of menthyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of menthyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranoside

There total 5 articles about menthyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranoside 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: 86.0%

(-)-menthol (2216-51-5) + (2R,3S,4S,5R,6R)-6-(acetoxymethyl)-3-iodotetrahydro-2H-pyran-2,4,5-triyl triacetate (113574-79-1) → menthyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranoside (1258282-08-4)

Guidance literature:

With copper(II) bis(trifluoromethanesulfonate); In 1,2-dichloro-ethane; at 60 ℃; for 1h; Solvent; Temperature; stereoselective reaction; Catalytic behavior; Inert atmosphere;

DOI:10.1016/j.tetlet.2016.01.035

Reference yield: 82.0%

(-)-menthol (2216-51-5) + D-glucal triacetate (2873-29-2) → menthyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranoside (1258282-08-4)

Guidance literature:

With [bis(acetoxy)iodo]benzene; iodine; In acetonitrile; at 20 ℃; diastereoselective reaction;

DOI:10.1055/s-0036-1588440

Reference yield:

(-)-menthol (2216-51-5) + 3,4,6-tri-O-acetyl-D-glucal → menthyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranoside (1258282-08-4) + C22H35IO8

Guidance literature:

With iodine; copper diacetate; In dichloromethane; at 10 - 20 ℃; for 5h; optical yield given as %de; Molecular sieve;

DOI:10.1016/j.carres.2010.08.020

upstream raw materials:

(-)-menthol

D-glucal triacetate

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