Octanoic acid (E)-(1S,5S,9R,15R,19R,21S,24S)-19-((R)-1-benzyloxy-ethyl)-1,15-dihydroxy-23-[1-methoxycarbonyl-meth-(E)-ylidene]-2,2-dimethyl-17-oxo-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,9R,15R,19R,21S,24S)-19-((R)-1-benzyloxy-ethyl)-1,15-dihydroxy-23-[1-methoxycarbonyl-meth-(E)-ylidene]-2,2-dimethyl-17-oxo-6,12,18,25,26-pentaoxa-tricyclo[19.3.1.1^5,9]hexacos-3-en-24-yl ester
• CAS No.: 218591-67-4
• Molecular Formula: C₄₃H₆₄O₁₃
• Molecular Weight: 788.973

Synonyms:

Chemical Property of Octanoic acid (E)-(1S,5S,9R,15R,19R,21S,24S)-19-((R)-1-benzyloxy-ethyl)-1,15-dihydroxy-23-[1-methoxycarbonyl-meth-(E)-ylidene]-2,2-dimethyl-17-oxo-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,9R,15R,19R,21S,24S)-19-((R)-1-benzyloxy-ethyl)-1,15-dihydroxy-23-[1-methoxycarbonyl-meth-(E)-ylidene]-2,2-dimethyl-17-oxo-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,9R,15R,19R,21S,24S)-19-((R)-1-benzyloxy-ethyl)-1,15-dihydroxy-23-[1-methoxycarbonyl-meth-(E)-ylidene]-2,2-dimethyl-17-oxo-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:

C53H82O14 → Octanoic acid (E)-(1S,5S,9R,15R,19R,21S,24S)-19-((R)-1-benzyloxy-ethyl)-1,15-dihydroxy-23-[1-methoxycarbonyl-meth-(E)-ylidene]-2,2-dimethyl-17-oxo-6,12,18,25,26-pentaoxa-tricyclo[19.3.1.15,9]hexacos-3-en-24-yl ester (218591-67-4)

Guidance literature:

With amberlyst-15 resin; In dichloromethane; at 20 ℃; for 72h;

DOI:10.1016/S0040-4039(98)01955-8

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,9R,15R,19R,21S,24S)-19-((R)-1-benzyloxy-ethyl)-1,15-dihydroxy-23-[1-methoxycarbonyl-meth-(E)-ylidene]-2,2-dimethyl-17-oxo-6,12,18,25,26-pentaoxa-tricyclo[19.3.1.15,9]hexacos-3-en-24-yl ester (218591-67-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / 2,4,6-trichlorobenzoylchloride, Et₃N, DMAP / CH₂Cl₂ / 20 °C

2: 85 percent / HF*pyridine / acetonitrile / 20 °C

3: Amberlyst-15 resin / CH₂Cl₂ / 72 h / 20 °C

With dmap; amberlyst-15 resin; 2,4,6-trichlorobenzoyl chloride; pyridine hydrogenfluoride; triethylamine; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(98)01955-8

Reference yield:

(R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-[2-((2R,7S,10R)-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-2-yl)-ethoxy]-pentanoic acid (218591-59-4) → Octanoic acid (E)-(1S,5S,9R,15R,19R,21S,24S)-19-((R)-1-benzyloxy-ethyl)-1,15-dihydroxy-23-[1-methoxycarbonyl-meth-(E)-ylidene]-2,2-dimethyl-17-oxo-6,12,18,25,26-pentaoxa-tricyclo[19.3.1.15,9]hexacos-3-en-24-yl ester (218591-67-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / 2,4,6-trichlorobenzoylchloride, Et₃N, DMAP / CH₂Cl₂ / 20 °C

2: 85 percent / HF*pyridine / acetonitrile / 20 °C

3: Amberlyst-15 resin / CH₂Cl₂ / 72 h / 20 °C

With dmap; amberlyst-15 resin; 2,4,6-trichlorobenzoyl chloride; pyridine hydrogenfluoride; triethylamine; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(98)01955-8

upstream raw materials:

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

(R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-[2-((2R,7S,10R)-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-2-yl)-ethoxy]-pentanoic acid

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