(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

Base Information

• Chemical Name: (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
• CAS No.: 608143-20-0
• Molecular Formula: C₅₅H₉₁NO₁₃Si
• Molecular Weight: 1002.41
• Mol file: 608143-20-0.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 1 articles about (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 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: 64.0%

(3S,4R,5R,6R,7R,9R,10S,11S,12S,13S,14R)-14-(benzyloxymethoxy)-6-O-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-3,5,7,9,11,13-hexamethyl-7-[(triethylsilyl)oxy]-10,12-{[(R)-2,4,6-trimethylbenzylidene]dioxy}hexadecen-4-ol (608143-19-7) → (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)

Guidance literature:

With osmium(VIII) oxide; oxone; sodium hydrogencarbonate; In N,N-dimethyl-formamide;

DOI:10.1002/anie.200351136

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:

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

Guidance literature:

Multi-step reaction with 3 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

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

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

DOI:10.1016/j.tet.2007.02.044

upstream raw materials:

(3S,4R,5R,6R,7R,9R,10S,11S,12S,13S,14R)-14-(benzyloxymethoxy)-6-O-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-3,5,7,9,11,13-hexamethyl-7-[(triethylsilyl)oxy]-10,12-{[(R)-2,4,6-trimethylbenzylidene]dioxy}hexadecen-4-ol

Downstream 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

(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