octanoic acid 19-(1-benzyloxy-ethyl)-11-(2-chloroacetoxy-1,1-dimethyl-ethyl)-1,15-dihydroxy-23-methoxycarbonylmethylene-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 19-(1-benzyloxy-ethyl)-11-(2-chloroacetoxy-1,1-dimethyl-ethyl)-1,15-dihydroxy-23-methoxycarbonylmethylene-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.: 263711-69-9
• Molecular Formula: C₄₉H₇₁ClO₁₆
• Molecular Weight: 951.546

Synonyms:octanoic acid 19-(1-benzyloxy-ethyl)-11-(2-chloroacetoxy-1,1-dimethyl-ethyl)-1,15-dihydroxy-23-methoxycarbonylmethylene-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 19-(1-benzyloxy-ethyl)-11-(2-chloroacetoxy-1,1-dimethyl-ethyl)-1,15-dihydroxy-23-methoxycarbonylmethylene-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

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Technology Process of octanoic acid 19-(1-benzyloxy-ethyl)-11-(2-chloroacetoxy-1,1-dimethyl-ethyl)-1,15-dihydroxy-23-methoxycarbonylmethylene-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 19-(1-benzyloxy-ethyl)-11-(2-chloroacetoxy-1,1-dimethyl-ethyl)-1,15-dihydroxy-23-methoxycarbonylmethylene-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: 62.0%

C65H103ClO17Si (263711-67-7) → octanoic acid 19-(1-benzyloxy-ethyl)-11-(2-chloroacetoxy-1,1-dimethyl-ethyl)-1,15-dihydroxy-23-methoxycarbonylmethylene-2,2-dimethyl-13,17-dioxo-6,12,18,25,26-pentaoxa-tricyclo[19.3.1.15,9]hexacos-3-en-24-yl ester (263711-69-9)

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)-3-(2-chloro-acetoxy)-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 (343601-38-7) → octanoic acid 19-(1-benzyloxy-ethyl)-11-(2-chloroacetoxy-1,1-dimethyl-ethyl)-1,15-dihydroxy-23-methoxycarbonylmethylene-2,2-dimethyl-13,17-dioxo-6,12,18,25,26-pentaoxa-tricyclo[19.3.1.15,9]hexacos-3-en-24-yl ester (263711-69-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / H₂ / Pd(OH)2 / ethyl acetate

2: 75 percent / Et₃N; 2,4,6-trichlorobenzoyl chloride; DMAP / toluene

3: 62 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 19-(1-benzyloxy-ethyl)-11-(2-chloroacetoxy-1,1-dimethyl-ethyl)-1,15-dihydroxy-23-methoxycarbonylmethylene-2,2-dimethyl-13,17-dioxo-6,12,18,25,26-pentaoxa-tricyclo[19.3.1.15,9]hexacos-3-en-24-yl ester (263711-69-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / Et₃N; 2,4,6-trichlorobenzoyl chloride; DMAP / toluene

2: 62 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:

C₆₅H₁₀₃ClO₁₇Si

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)-3-(2-chloro-acetoxy)-1-((2S,6S,7S,10R)-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-2-ylmethyl)-2,2-dimethyl-propyl] ester

(S)-3-(tert-Butyl-dimethyl-silanyloxy)-pentanedioic acid (S)-3-(2-chloro-acetoxy)-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

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