Octanoic acid (E)-(1S,5S,9S,11S,15R,19R,21S,24S)-19-((R)-1-benzyloxy-ethyl)-11-tert-butyl-1,15-dihydroxy-23-[1-methoxycarbonyl-meth-(E)-ylidene]-2,2-dimethyl-13,17-dioxo-6,12,18,25,26-pentaoxa-tricyclo[19.3.1.1^5,9]hexacos-3-en-24-yl ester

Base Information

• Chemical Name: Octanoic acid (E)-(1S,5S,9S,11S,15R,19R,21S,24S)-19-((R)-1-benzyloxy-ethyl)-11-tert-butyl-1,15-dihydroxy-23-[1-methoxycarbonyl-meth-(E)-ylidene]-2,2-dimethyl-13,17-dioxo-6,12,18,25,26-pentaoxa-tricyclo[19.3.1.1^5,9]hexacos-3-en-24-yl ester
• CAS No.: 263711-70-2
• Molecular Formula: C₄₇H₇₀O₁₄
• Molecular Weight: 859.064

Synonyms:Octanoic acid (E)-(1S,5S,9S,11S,15R,19R,21S,24S)-19-((R)-1-benzyloxy-ethyl)-11-tert-butyl-1,15-dihydroxy-23-[1-methoxycarbonyl-meth-(E)-ylidene]-2,2-dimethyl-13,17-dioxo-6,12,18,25,26-pentaoxa-tricyclo[19.3.1.1^5,9]hexacos-3-en-24-yl ester

Chemical Property of Octanoic acid (E)-(1S,5S,9S,11S,15R,19R,21S,24S)-19-((R)-1-benzyloxy-ethyl)-11-tert-butyl-1,15-dihydroxy-23-[1-methoxycarbonyl-meth-(E)-ylidene]-2,2-dimethyl-13,17-dioxo-6,12,18,25,26-pentaoxa-tricyclo[19.3.1.1^5,9]hexacos-3-en-24-yl ester

Chemical Property:

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Technology Process of Octanoic acid (E)-(1S,5S,9S,11S,15R,19R,21S,24S)-19-((R)-1-benzyloxy-ethyl)-11-tert-butyl-1,15-dihydroxy-23-[1-methoxycarbonyl-meth-(E)-ylidene]-2,2-dimethyl-13,17-dioxo-6,12,18,25,26-pentaoxa-tricyclo[19.3.1.1^5,9]hexacos-3-en-24-yl ester

There total 4 articles about Octanoic acid (E)-(1S,5S,9S,11S,15R,19R,21S,24S)-19-((R)-1-benzyloxy-ethyl)-11-tert-butyl-1,15-dihydroxy-23-[1-methoxycarbonyl-meth-(E)-ylidene]-2,2-dimethyl-13,17-dioxo-6,12,18,25,26-pentaoxa-tricyclo[19.3.1.1^5,9]hexacos-3-en-24-yl ester 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: 79.0%

C63H102O15Si (263711-68-8) → Octanoic acid (E)-(1S,5S,9S,11S,15R,19R,21S,24S)-19-((R)-1-benzyloxy-ethyl)-11-tert-butyl-1,15-dihydroxy-23-[1-methoxycarbonyl-meth-(E)-ylidene]-2,2-dimethyl-13,17-dioxo-6,12,18,25,26-pentaoxa-tricyclo[19.3.1.15,9]hexacos-3-en-24-yl ester (263711-70-2)

Guidance literature:

With pyridine; hydrogen fluoride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(99)02195-4

Reference yield:

(S)-3-(tert-Butyl-dimethyl-silanyloxy)-pentanedioic acid (S)-1-((2S,6S,7S,10R)-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-2-ylmethyl)-2,2-dimethyl-propyl ester (R)-1-naphthalen-1-yl-ethyl ester → Octanoic acid (E)-(1S,5S,9S,11S,15R,19R,21S,24S)-19-((R)-1-benzyloxy-ethyl)-11-tert-butyl-1,15-dihydroxy-23-[1-methoxycarbonyl-meth-(E)-ylidene]-2,2-dimethyl-13,17-dioxo-6,12,18,25,26-pentaoxa-tricyclo[19.3.1.15,9]hexacos-3-en-24-yl ester (263711-70-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / H₂ / Pd(OH)2 / ethyl acetate

2: 70 percent / Et₃N; 2,4,6-trichlorobenzoyl chloride; DMAP / toluene

3: 79 percent / HF; pyridine / tetrahydrofuran

With pyridine; dmap; 2,4,6-trichlorobenzoyl chloride; hydrogen fluoride; hydrogen; triethylamine; palladium dihydroxide; In tetrahydrofuran; ethyl acetate; toluene; 1: Hydrogenolysis / 2: Esterification / 3: Cyclization;

DOI:10.1016/S0040-4039(99)02195-4

Reference yield:

Octanoic acid (2S,3S,6S)-6-((2R,3R)-3-benzyloxy-2-hydroxy-butyl)-2-((E)-1,1-dimethyl-4-oxo-but-2-enyl)-2-hydroxy-4-[1-methoxycarbonyl-meth-(E)-ylidene]-tetrahydro-pyran-3-yl ester (206255-51-8) → Octanoic acid (E)-(1S,5S,9S,11S,15R,19R,21S,24S)-19-((R)-1-benzyloxy-ethyl)-11-tert-butyl-1,15-dihydroxy-23-[1-methoxycarbonyl-meth-(E)-ylidene]-2,2-dimethyl-13,17-dioxo-6,12,18,25,26-pentaoxa-tricyclo[19.3.1.15,9]hexacos-3-en-24-yl ester (263711-70-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / Et₃N; 2,4,6-trichlorobenzoyl chloride; DMAP / toluene

2: 79 percent / HF; pyridine / tetrahydrofuran

With pyridine; dmap; 2,4,6-trichlorobenzoyl chloride; hydrogen fluoride; triethylamine; In tetrahydrofuran; toluene; 1: Esterification / 2: Cyclization;

DOI:10.1016/S0040-4039(99)02195-4

upstream raw materials:

C₆₃H₁₀₂O₁₅Si

Octanoic acid (2S,3S,6S)-6-((2R,3R)-3-benzyloxy-2-hydroxy-butyl)-2-((E)-1,1-dimethyl-4-oxo-but-2-enyl)-2-hydroxy-4-[1-methoxycarbonyl-meth-(E)-ylidene]-tetrahydro-pyran-3-yl ester

(S)-3-(tert-Butyl-dimethyl-silanyloxy)-pentanedioic acid mono-[(S)-1-((2S,6S,7S,10R)-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-2-ylmethyl)-2,2-dimethyl-propyl] ester

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