cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-α-D-glucopyranoside

Base Information

• Chemical Name: cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-α-D-glucopyranoside
• CAS No.: 84207-52-3
• Molecular Formula: C₃₃H₃₉IO₅
• Molecular Weight: 642.574
• Mol file: 84207-52-3.mol

Synonyms:cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-α-D-glucopyranoside

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

Chemical Property:

Purity/Quality:

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

There total 4 articles about cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-α-D-glucopyranoside 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%

cyclohexanol (108-93-0) + phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-1-thio-α-D-mannopyranoside (653575-98-5) → cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-α-D-glucopyranoside (84207-52-3)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In dichloromethane; at -78 - -40 ℃;

DOI:10.1055/s-2003-42066

Reference yield: 67.0%

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) + cyclohexanol (108-93-0) → cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-α-D-glucopyranoside (84207-52-3) + cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-β-D-glucopyranoside (84207-53-4)

Guidance literature:

3,4,6-tri-O-benzyl-D-glucal; cyclohexanol; With triphenylphosphine; In dichloromethane; at 20 ℃; for 0.333333h; Inert atmosphere;

With N-iodo-succinimide; In dichloromethane; at -40 ℃; for 12h; Overall yield = 90 %; stereoselective reaction; Inert atmosphere;

DOI:10.1021/acs.joc.5b01542

Reference yield:

(E)-(2R,3R,4R)-1,3,4-Tris-benzyloxy-6-cyclohexyloxy-hex-5-en-2-ol (82252-29-7,82309-83-9) → cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-α-D-glucopyranoside (84207-52-3) + cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-β-D-glucopyranoside (84207-53-4)

Guidance literature:

With N-iodo-succinimide; In various solvent(s); at -78 ℃; for 3h;

DOI:10.1246/cl.1982.1525

upstream raw materials:

(E)-(2R,3R,4R)-1,3,4-Tris-benzyloxy-6-cyclohexyloxy-hex-5-en-2-ol

cyclohexanol

phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-1-thio-α-D-mannopyranoside

2,3,5-tri-O-benzyl-D-arabinofuranose