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

Base Information

Chemical Name:(9S)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)-9,11-O-[(R)-2,4,6-trimethylbenzylidene]erythronolide B
CAS No.:188786-47-2
Molecular Formula:C₄₁H₆₇NO₁₁
Molecular Weight:749.983
Hs Code.:

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

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

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

There total 22 articles about (9S)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)-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: 93.0%

: 608143-21-1
(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

: 188786-47-2
(9S)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)-9,11-O-[(R)-2,4,6-trimethylbenzylidene]erythronolide B

Guidance literature:: With tetrabutyl ammonium fluoride; In N,N-dimethyl-formamide;
DOI:10.1002/anie.200351136

Reference yield: 61.0%

: 188786-37-0
(9S)-9,11-O-[(R)-2,4,6-trimethylbenzylidene]-9-dihydroerythronolide B

: C₁₄H₂₁N₃O₄S

: 188786-47-2
(9S)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)-9,11-O-[(R)-2,4,6-trimethylbenzylidene]erythronolide B

Guidance literature:: With 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; toluene; at 0 ℃; for 1h;
DOI:10.1016/j.tet.2007.02.044

Reference yield:

: 608143-20-0
(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

: 188786-47-2
(9S)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)-9,11-O-[(R)-2,4,6-trimethylbenzylidene]erythronolide B

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