cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranoside

Base Information

• Chemical Name: cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranoside
• CAS No.: 82252-30-0
• Molecular Formula: C₃₃H₄₀O₅
• Molecular Weight: 516.678
• Mol file: 82252-30-0.mol

Synonyms:cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranoside

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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

There total 10 articles about cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranoside 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: 81.0%

3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose (160549-11-1) + cyclohexanol (108-93-0) → cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranoside (82252-31-1) + cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranoside (82252-30-0)

Guidance literature:

With pyrrolidine hydrochloride; In toluene; at 100 ℃; for 5h; diastereoselective reaction; Inert atmosphere;

DOI:10.1039/c8ob00423d

Reference yield:

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) + cyclohexanol (108-93-0) → cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranoside (82252-31-1) + cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranoside (82252-30-0)

Guidance literature:

cyclohexanol; With triphenyl phosphite; N-iodo-succinimide; In dichloromethane; at 20 ℃; for 0.333333h; Inert atmosphere;

3,4,6-tri-O-benzyl-D-glucal; In acetic acid; at 20 ℃; for 3h; Overall yield = 87 %; stereoselective reaction; Inert atmosphere;

DOI:10.1021/acs.joc.5b01542

Reference yield:

3,4,6-Tri-O-benzyl-2-deoxy-α-D-glucopyranosyl fluoride (163916-60-7) + cyclohexanol (108-93-0) → cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranoside (82252-31-1) + cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranoside (82252-30-0)

Guidance literature:

With 4 A molecular sieve; potassium carbonate; ytterbium(III) triflate; In acetonitrile; at -15 ℃; for 2h; Yield given. Yields of byproduct given;

DOI:10.1021/jo00106a002

upstream raw materials:

(Z)-(2R,3R,4R)-6-cyclohexyloxy-1,3,4-tribenzyloxy-5-hexen-2-ol

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

3,4,6-Tri-O-benzyl-2-deoxy-α-D-glucopyranosyl fluoride

cyclohexanol