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

Base Information

• Chemical Name: 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
• CAS No.: 944740-95-8
• Molecular Formula: C₄₇H₈₃NO₁₂Si
• Molecular Weight: 882.261
• Mol file: 944740-95-8.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 1 articles about 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 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) → 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)

Guidance literature:

With perchloric acid; hydrogen; palladium on activated charcoal; In tetrahydrofuran; water;

DOI:10.1002/anie.200351136

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)-β-D-desosaminyl)-9,11-O-[(R)-2,4,6-trimethylbenzylidene]erythronolide B (188786-47-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.0 mg / triethylamine; 4-(dimethylamino)pyridine; 2,4,6-trichlorobenzoylchloride / toluene / 0.5 h / 20 °C

2: 93 percent / tetrabutylammonium fluoride / dimethylformamide / 3 h / 20 °C

With dmap; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; triethylamine; In 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

upstream raw materials:

(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-α-D-desosaminyl)oxy]-6-O-triethylsilyl-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