(1R,2R,4R,8R,9R,10R,13R,14S,18S,19S)-10-ethyl-9-hydroxy-2,4,9,13,18,19-hexamethyl-16-phenyl-2-[(triethylsilyl)oxy]-7,11,15,17-tetraoxa-6-azatricyclo[12.3.1.1^5,8]nonadec-5-en-12-one

Base Information

• Chemical Name: (1R,2R,4R,8R,9R,10R,13R,14S,18S,19S)-10-ethyl-9-hydroxy-2,4,9,13,18,19-hexamethyl-16-phenyl-2-[(triethylsilyl)oxy]-7,11,15,17-tetraoxa-6-azatricyclo[12.3.1.1^5,8]nonadec-5-en-12-one
• CAS No.: 863663-28-9
• Molecular Formula: C₃₄H₅₅NO₇Si
• Molecular Weight: 617.899

Synonyms:(1R,2R,4R,8R,9R,10R,13R,14S,18S,19S)-10-ethyl-9-hydroxy-2,4,9,13,18,19-hexamethyl-16-phenyl-2-[(triethylsilyl)oxy]-7,11,15,17-tetraoxa-6-azatricyclo[12.3.1.1^5,8]nonadec-5-en-12-one

Chemical Property of (1R,2R,4R,8R,9R,10R,13R,14S,18S,19S)-10-ethyl-9-hydroxy-2,4,9,13,18,19-hexamethyl-16-phenyl-2-[(triethylsilyl)oxy]-7,11,15,17-tetraoxa-6-azatricyclo[12.3.1.1^5,8]nonadec-5-en-12-one

Chemical Property:

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Technology Process of (1R,2R,4R,8R,9R,10R,13R,14S,18S,19S)-10-ethyl-9-hydroxy-2,4,9,13,18,19-hexamethyl-16-phenyl-2-[(triethylsilyl)oxy]-7,11,15,17-tetraoxa-6-azatricyclo[12.3.1.1^5,8]nonadec-5-en-12-one

There total 6 articles about (1R,2R,4R,8R,9R,10R,13R,14S,18S,19S)-10-ethyl-9-hydroxy-2,4,9,13,18,19-hexamethyl-16-phenyl-2-[(triethylsilyl)oxy]-7,11,15,17-tetraoxa-6-azatricyclo[12.3.1.1^5,8]nonadec-5-en-12-one 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: 78.0%

3,5-O-benzylidene-2,4,7-trideoxy-6-C-((2R)-2-{(4S,5R)-5-[(2R)-2-hydroxy-1,1-dimethylbutyl]-4-methyl-4,5-dihydroisoxazol-3-yl}propyl)-2,4-dimethyl-3,5-O-(1-methylethylidene)-6-O-(triethylsilyl)-L-glycero-D-gulo-heptitol (863663-27-8) → (1R,2R,4R,8R,9R,10R,13R,14S,18S,19S)-10-ethyl-9-hydroxy-2,4,9,13,18,19-hexamethyl-16-phenyl-2-[(triethylsilyl)oxy]-7,11,15,17-tetraoxa-6-azatricyclo[12.3.1.15,8]nonadec-5-en-12-one (863663-28-9)

Guidance literature:

3,5-O-benzylidene-2,4,7-trideoxy-6-C-((2R)-2-{(4S,5R)-5-[(2R)-2-hydroxy-1,1-dimethylbutyl]-4-methyl-4,5-dihydroisoxazol-3-yl}propyl)-2,4-dimethyl-3,5-O-(1-methylethylidene)-6-O-(triethylsilyl)-L-glycero-D-gulo-heptitol; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 0 ℃; for 0.5h;

With dmap; In toluene; at 50 ℃; for 3h;

DOI:10.1021/jo901817b

Reference yield:

C41H58Cl3NO9Si → (1R,2R,4R,8R,9R,10R,13R,14S,18S,19S)-10-ethyl-9-hydroxy-2,4,9,13,18,19-hexamethyl-16-phenyl-2-[(triethylsilyl)oxy]-7,11,15,17-tetraoxa-6-azatricyclo[12.3.1.15,8]nonadec-5-en-12-one (863663-28-9)

Guidance literature:

With dmap; triethylamine; In tetrahydrofuran; toluene; at 50 ℃; for 0.75h;

DOI:10.1002/anie.200500172

Reference yield:

3,5-O-benzylidene-1,4,6-trideoxy-2-C-((2R)-2-{(4S,5R)-5-[(1R,2R)-1,2-dihydroxy-1-methylbutyl]-4-methyl-4,5-dihydroisoxazol-3-yl}propyl)-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol (863663-36-9) → (1R,2R,4R,8R,9R,10R,13R,14S,18S,19S)-10-ethyl-9-hydroxy-2,4,9,13,18,19-hexamethyl-16-phenyl-2-[(triethylsilyl)oxy]-7,11,15,17-tetraoxa-6-azatricyclo[12.3.1.15,8]nonadec-5-en-12-one (863663-28-9)

Guidance literature:

Multi-step reaction with 4 steps

1: TEMPO; KBr; aq. carbonate buffer / NaOCl / CH₂Cl₂ / 0.5 h / 0 °C / pH 8.6

2: 190 mg / 2-methyl-2-butene; NaClO₂; aq. citrate phosphate buffer / 2-methyl-propan-2-ol / 0.5 h / 0 °C / pH 3.8

3: Et₃N / tetrahydrofuran / 0 - 20 °C

4: 103 mg / Et₃N; DMAP / tetrahydrofuran; toluene / 0.75 h / 50 °C

With dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium chlorite; 2-methyl-but-2-ene; Carbonate buffer; citrate phosphate buffer; triethylamine; potassium bromide; sodium hypochlorite; In tetrahydrofuran; dichloromethane; toluene; tert-butyl alcohol;

DOI:10.1002/anie.200500172

upstream raw materials:

3,5-O-benzylidene-1,4,6-trideoxy-2-C-((2R)-2-{(4S,5R)-5-[(1R,2R)-1,2-dihydroxy-1-methylbutyl]-4-methyl-4,5-dihydroisoxazol-3-yl}propyl)-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol

3,5-O-benzylidene-2,4,7-trideoxy-6-C-((2R)-2-{(4S,5R)-5-[(2R)-2-hydroxy-1,1-dimethylbutyl]-4-methyl-4,5-dihydroisoxazol-3-yl}propyl)-2,4-dimethyl-3,5-O-(1-methylethylidene)-6-O-(triethylsilyl)-L-glycero-D-gulo-heptitol

3,5-O-benzylidene-7-O-[tert-butyl(dimethyl)silyl]-1,4,6-trideoxy-4,6-dimethyl-2-C-((2R)-2-{(4S,5R)-4-methyl-5-[(1Z)-1-methylbut-1-en-1-yl]-4,5-dihydroisoxazol-3-yl}propyl)-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol

3,5-O-benzylidene-7-O-[tert-butyl(dimethyl)silyl]-1,4,6-trideoxy-2-C-((2R)-2-{(4S,5R)-5-[(2R)-2-hydroxy-1,1-dimethylbutyl]-4-methyl-4,5-dihydroisoxazol-3-yl}propyl)-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol

Downstream raw materials:

erythronolide A

(1R,2R,4R,8R,9R,10R,13R,14S,18S,19S)-10-ethyl-2,9-dihydroxy-2,4,9,13,18,19-hexamethyl-16-phenyl-7,11,15,17-tetraoxa-6-azatricyclo[12.3.1.1^5,8]nonadec-5-en-12-one

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