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

Base Information

• Chemical Name: 5-(4-O-benzyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A?11,12-cyclic carbonate
• CAS No.: 1415663-31-8
• Molecular Formula: C₃₈H₅₇NO₁₂
• Molecular Weight: 719.87
• Mol file: 1415663-31-8.mol

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

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

There total 22 articles about 5-(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: 77.0%

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) → 5-(4-O-benzyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A?11,12-cyclic carbonate (1415663-31-8)

Guidance literature:

In methanol; at 50 ℃; for 40h; Inert atmosphere;

DOI:10.1016/j.bmcl.2012.10.064

Reference yield:

methyl 2,3-di-O-benzoyl-4-O-benzyl-6-deoxy-α-D-glucopyranoside (131589-94-1) → 5-(4-O-benzyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A?11,12-cyclic carbonate (1415663-31-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sodium methylate / dichloromethane; methanol / 10 h / pH 10

2.1: pyridine; p-toluenesulfonyl chloride; dmap / 20 - 80 °C / Inert atmosphere

3.1: sodium methylate / dichloromethane; methanol / 48 h / 0 - 5 °C / Inert atmosphere

4.1: water / 6 h / Inert atmosphere; Heating

5.1: pyridine / 3 h / 0 - 20 °C / Inert atmosphere

6.1: acetic acid; sulfuric acid / 48 h / Inert atmosphere

7.1: boron trifluoride diethyl etherate / dichloromethane / 48 h / 30 °C / Inert atmosphere; Molecular sieve

8.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere

9.1: N-iodo-succinimide / dichloromethane / 0.17 h / Inert atmosphere; Molecular sieve; Darkness; Cooling

9.2: 10 h / 20 °C / Inert atmosphere

10.1: methanol / 40 h / 50 °C / Inert atmosphere

With pyridine; dmap; N-iodo-succinimide; sulfuric acid; boron trifluoride diethyl etherate; sodium methylate; sodium hydride; acetic acid; p-toluenesulfonyl chloride; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2012.10.064

Reference yield:

methyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranoside (1415663-21-6) → 5-(4-O-benzyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A?11,12-cyclic carbonate (1415663-31-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: acetic acid; sulfuric acid / 48 h / Inert atmosphere

2.1: boron trifluoride diethyl etherate / dichloromethane / 48 h / 30 °C / Inert atmosphere; Molecular sieve

3.1: N-iodo-succinimide / dichloromethane / 0.17 h / Inert atmosphere; Molecular sieve; Darkness; Cooling

3.2: 10 h / 20 °C / Inert atmosphere

4.1: methanol / 40 h / 50 °C / Inert atmosphere

With N-iodo-succinimide; sulfuric acid; boron trifluoride diethyl etherate; acetic acid; In methanol; dichloromethane;

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