(9S)-9-dihydro-5-O-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-6-O-triethylsilyl-9,11-O-[(R)-2,4,6-trimethylbenzylidene]erythronolide B

Base Information

• Chemical Name: (9S)-9-dihydro-5-O-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-6-O-triethylsilyl-9,11-O-[(R)-2,4,6-trimethylbenzylidene]erythronolide B
• CAS No.: 608143-21-1
• Molecular Formula: C₄₇H₈₁NO₁₁Si
• Molecular Weight: 864.246
• Mol file: 608143-21-1.mol

Synonyms:(9S)-9-dihydro-5-O-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-6-O-triethylsilyl-9,11-O-[(R)-2,4,6-trimethylbenzylidene]erythronolide B

Chemical Property of (9S)-9-dihydro-5-O-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-6-O-triethylsilyl-9,11-O-[(R)-2,4,6-trimethylbenzylidene]erythronolide B

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (9S)-9-dihydro-5-O-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-6-O-triethylsilyl-9,11-O-[(R)-2,4,6-trimethylbenzylidene]erythronolide B

There total 2 articles about (9S)-9-dihydro-5-O-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-6-O-triethylsilyl-9,11-O-[(R)-2,4,6-trimethylbenzylidene]erythronolide B 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:

(2R,3S,4S,5R,6R,7R,9S,10S,11S,12S,13R)-13-(benzyloxymethoxy)-6-[triethylsilyloxy]-5-O-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-2,3,6,8,10,12-hexamethyl-9,11-{[(R)-2,4,6-trimethylbenzylidene]dioxy}pentadecanoic acid (608143-20-0) → (9S)-9-dihydro-5-O-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-6-O-triethylsilyl-9,11-O-[(R)-2,4,6-trimethylbenzylidene]erythronolide B (608143-21-1)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen; aq. HClO₄ / Pd/C / tetrahydrofuran; dimethylformamide / 6 h

2: 2.0 mg / triethylamine; 4-(dimethylamino)pyridine; 2,4,6-trichlorobenzoylchloride / toluene / 0.5 h / 20 °C

With dmap; perchloric acid; 2,4,6-trichlorobenzoyl chloride; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tet.2007.02.044

Reference yield:

5-(4-dimethylamino-3-methoxycarbonyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-3-hydroxy-8-[6-(2-hydroxy-1-methyl-butyl)-5-methyl-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxan-4-yl]-2,4,6-trimethyl-6-triethylsilanyloxy-nonanoic acid (944740-95-8) → (9S)-9-dihydro-5-O-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-6-O-triethylsilyl-9,11-O-[(R)-2,4,6-trimethylbenzylidene]erythronolide B (608143-21-1)

Guidance literature:

With dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine;

DOI:10.1002/anie.200351136

Reference yield: 93.0%

(9S)-9-dihydro-5-O-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-6-O-triethylsilyl-9,11-O-[(R)-2,4,6-trimethylbenzylidene]erythronolide B (608143-21-1) → (9S)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)-9,11-O-[(R)-2,4,6-trimethylbenzylidene]erythronolide B (188786-47-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In N,N-dimethyl-formamide;

DOI:10.1002/anie.200351136

upstream raw materials:

5-(4-dimethylamino-3-methoxycarbonyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-3-hydroxy-8-[6-(2-hydroxy-1-methyl-butyl)-5-methyl-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxan-4-yl]-2,4,6-trimethyl-6-triethylsilanyloxy-nonanoic acid

(2R,3S,4S,5R,6R,7R,9S,10S,11S,12S,13R)-13-(benzyloxymethoxy)-6-[triethylsilyloxy]-5-O-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-2,3,6,8,10,12-hexamethyl-9,11-{[(R)-2,4,6-trimethylbenzylidene]dioxy}pentadecanoic acid

Downstream raw materials:

(9S)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)-9,11-O-[(R)-2,4,6-trimethylbenzylidene]erythronolide B

(9S)-3-O-(4-O-(tert-butyldimethylsilyl)-α-L-cladinosyl)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)-9,11-O-[(R)-2,4,6-trimethylbenzylidene]erythronolide B

C₄₇H₇₇NO₁₄