5-(2-O-benzoyl-4-O-benzyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A 11,12-cyclic carbonate

Base Information

• Chemical Name: 5-(2-O-benzoyl-4-O-benzyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A 11,12-cyclic carbonate
• CAS No.: 1415663-30-7
• Molecular Formula: C₄₅H₆₁NO₁₃
• Molecular Weight: 823.978
• Mol file: 1415663-30-7.mol

Synonyms:5-(2-O-benzoyl-4-O-benzyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A 11,12-cyclic carbonate

Chemical Property of 5-(2-O-benzoyl-4-O-benzyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A 11,12-cyclic carbonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(2-O-benzoyl-4-O-benzyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A 11,12-cyclic carbonate

There total 22 articles about 5-(2-O-benzoyl-4-O-benzyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A 11,12-cyclic carbonate 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: 40.0%

11,12-carbonate-11,12-dideoxy-5-hydroxyl-3-oxo-6-O-methyl-erythronolide A (1415663-19-2) + 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-D-glucopyranosyl fluoride → 5-(2-O-benzoyl-4-O-benzyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A 11,12-cyclic carbonate (1415663-30-7)

Guidance literature:

2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-D-glucopyranosyl fluoride; With bis(cyclopentadienyl)hafnium dichloride; silver perchlorate; In dichloromethane; for 0.166667h; Inert atmosphere; Molecular sieve; Darkness;

11,12-carbonate-11,12-dideoxy-5-hydroxyl-3-oxo-6-O-methyl-erythronolide A; With 2,6-di-tert-butyl-pyridine; In dichloromethane; at 35 - 40 ℃; for 12h;

DOI:10.1016/j.bmcl.2012.10.064

Reference yield: 30.0%

2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranosyl trichloroacetimidate (1415663-28-3) + 11,12-carbonate-11,12-dideoxy-5-hydroxyl-3-oxo-6-O-methyl-erythronolide A (1415663-19-2) → 5-(2-O-benzoyl-4-O-benzyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A 11,12-cyclic carbonate (1415663-30-7)

Guidance literature:

2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranosyl trichloroacetimidate; 11,12-carbonate-11,12-dideoxy-5-hydroxyl-3-oxo-6-O-methyl-erythronolide A; In dichloromethane; at -35 ℃; for 0.25h; Inert atmosphere; Molecular sieve;

With triethylsilyl trifluoromethyl sulfonate; In dichloromethane; for 2h; Inert atmosphere;

DOI:10.1016/j.bmcl.2012.10.064

Reference yield: 16.0%

ethyl 2-O-benzoyl-3,6-dideoxy-3-dimethylamino-1-thio-β-D-glucopyranoside (1415663-26-1) + 11,12-carbonate-11,12-dideoxy-5-hydroxyl-3-oxo-6-O-methyl-erythronolide A (1415663-19-2) → 5-(2-O-benzoyl-4-O-benzyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A 11,12-cyclic carbonate (1415663-30-7)

Guidance literature:

ethyl 2-O-benzoyl-3,6-dideoxy-3-dimethylamino-1-thio-β-D-glucopyranoside; 11,12-carbonate-11,12-dideoxy-5-hydroxyl-3-oxo-6-O-methyl-erythronolide A; With N-iodo-succinimide; In dichloromethane; for 0.166667h; Inert atmosphere; Molecular sieve; Darkness; Cooling;

With 2,6-di-tert-butyl-pyridine; silver trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 10h; Inert atmosphere;

DOI:10.1016/j.bmcl.2012.10.064

upstream raw materials:

benzaldehyde dimethyl acetal

methyl 2,3-di-O-benzoyl-4-O-benzyl-α-D-glucopyranoside

methyl 2,3-di-O-benzoyl-4-O-benzyl-6-bromo-6-deoxy-α-D-glucopyranoside

methyl 2,3-di-O-benzoyl-4-O-benzyl-6-deoxy-α-D-glucopyranoside

Downstream raw materials:

5-(4-O-benzyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A?11,12-cyclic carbonate