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

Base Information

• Chemical Name: cyclohexyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranoside
• CAS No.: 95475-52-8
• Molecular Formula: C₁₈H₂₇IO₈
• Molecular Weight: 498.312
• Mol file: 95475-52-8.mol

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

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

Chemical Property:

Purity/Quality:

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

There total 4 articles about cyclohexyl 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: 88.0%

cyclohexanol (108-93-0) + D-glucal triacetate (2873-29-2) → cyclohexyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranoside (95475-52-8)

Guidance literature:

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

DOI:10.1055/s-0036-1588440

Reference yield: 74.0%

[bis(acetoxy)iodo]benzene (3240-34-4) + cyclohexanol (108-93-0) + D-glucal triacetate (2873-29-2) → cyclohexyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranoside (95475-52-8) + (2R,3S,4S,5R,6R)-6-(acetoxymethyl)-3-iodotetrahydro-2H-pyran-2,4,5-triyl triacetate (113574-79-1)

Guidance literature:

With iodine; In acetonitrile; at 20 ℃; diastereoselective reaction;

DOI:10.1055/s-0036-1588440

Reference yield:

3,4,6-tri-O-acetyl-D-glucal + cyclohexanol (108-93-0) → cyclohexyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranoside (95475-52-8) + C18H27IO8 (95475-53-9)

Guidance literature:

With iodine; copper diacetate; In dichloromethane; at 10 - 20 ℃; for 3h; optical yield given as %de; stereoselective reaction; Molecular sieve;

DOI:10.1016/j.carres.2010.08.020

upstream raw materials:

cyclohexanol

D-glucal triacetate

[bis(acetoxy)iodo]benzene