6-O-benzyl-O-(3,4,6-tri-O-acetyl-2-deoxy-2-azido-α-D-glucopyranosyl)-(1→1)-2,3:4,5-di-O-cyclohexylidene-D-myo-inositol

Base Information

• Chemical Name: 6-O-benzyl-O-(3,4,6-tri-O-acetyl-2-deoxy-2-azido-α-D-glucopyranosyl)-(1→1)-2,3:4,5-di-O-cyclohexylidene-D-myo-inositol
• CAS No.: 418785-06-5
• Molecular Formula: C₃₇H₄₉N₃O₁₃
• Molecular Weight: 743.808
• Mol file: 418785-06-5.mol

Synonyms:6-O-benzyl-O-(3,4,6-tri-O-acetyl-2-deoxy-2-azido-α-D-glucopyranosyl)-(1→1)-2,3:4,5-di-O-cyclohexylidene-D-myo-inositol

Chemical Property of 6-O-benzyl-O-(3,4,6-tri-O-acetyl-2-deoxy-2-azido-α-D-glucopyranosyl)-(1→1)-2,3:4,5-di-O-cyclohexylidene-D-myo-inositol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-O-benzyl-O-(3,4,6-tri-O-acetyl-2-deoxy-2-azido-α-D-glucopyranosyl)-(1→1)-2,3:4,5-di-O-cyclohexylidene-D-myo-inositol

There total 14 articles about 6-O-benzyl-O-(3,4,6-tri-O-acetyl-2-deoxy-2-azido-α-D-glucopyranosyl)-(1→1)-2,3:4,5-di-O-cyclohexylidene-D-myo-inositol 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%

(-)-6-O-benzyl-2,3:4,5-di-O-cyclohexylidene-myo-inositol (124601-98-5) + 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-glucopyranosyl trichloroacetimidate (145840-43-3) → 6-O-benzyl-O-(3,4,6-tri-O-acetyl-2-deoxy-2-azido-α-D-glucopyranosyl)-(1→1)-2,3:4,5-di-O-cyclohexylidene-D-myo-inositol (418785-06-5)

Guidance literature:

(-)-6-O-benzyl-2,3:4,5-di-O-cyclohexylidene-myo-inositol; 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-glucopyranosyl trichloroacetimidate; In dichloromethane; at -20 - 20 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 ℃; for 1h; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.carres.2017.10.014

Reference yield: 44.0%

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl chloride (67817-20-3) + (-)-6-O-benzyl-2,3:4,5-di-O-cyclohexylidene-myo-inositol (124601-98-5) → 6-O-benzyl-O-(3,4,6-tri-O-acetyl-2-deoxy-2-azido-α-D-glucopyranosyl)-(1→1)-2,3:4,5-di-O-cyclohexylidene-D-myo-inositol (418785-06-5)

Guidance literature:

With diisopropyl-2,6-methyl-4-pyridine; silver trifluoromethanesulfonate; In diethyl ether; dichloromethane;

DOI:10.1021/ja017891a

Reference yield: 44.0%

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl chloride (67817-20-3) + (-)-6-O-benzyl-2,3:4,5-di-O-cyclohexylidene-myo-inositol (124601-98-5) → 6-O-benzyl-O-(3,4,6-tri-O-acetyl-2-deoxy-2-azido-α-D-glucopyranosyl)-(1→1)-2,3:4,5-di-O-cyclohexylidene-D-myo-inositol (418785-06-5) + C37H49N3O13

Guidance literature:

With diisopropyl-2,6-methyl-4-pyridine; silver trifluoromethanesulfonate; In dichloromethane;

DOI:10.1016/S0968-0896(03)00154-8

upstream raw materials:

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl chloride

(-)-6-O-benzyl-2,3:4,5-di-O-cyclohexylidene-myo-inositol

cyclohexanone

3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-glucopyranosyl trichloroacetimidate

Downstream raw materials:

1L-1-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-myo-inositol

diethylphophoryl cyanide

1-D-myo-inosityl-2-deoxy-2-(N-acetamido-L-cysteinamido)-α-D-glucopyranoside

Acetic acid (1S,2S,3S,4R,5S,6S)-2,3,4-triacetoxy-5-benzyloxy-6-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-cyclohexyl ester