(1R,9S,12S,14S,24R,27R)-1,14-Dihydroxy-12-[(R)-2-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-ethyl]-27-methyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0^4,9]octacosane-2,3,10,20-tetraone

Base Information

• Chemical Name: (1R,9S,12S,14S,24R,27R)-1,14-Dihydroxy-12-[(R)-2-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-ethyl]-27-methyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0^4,9]octacosane-2,3,10,20-tetraone
• CAS No.: 137299-02-6
• Molecular Formula: C₃₆H₅₉NO₁₀
• Molecular Weight: 665.865

Synonyms:

Chemical Property of (1R,9S,12S,14S,24R,27R)-1,14-Dihydroxy-12-[(R)-2-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-ethyl]-27-methyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0^4,9]octacosane-2,3,10,20-tetraone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,9S,12S,14S,24R,27R)-1,14-Dihydroxy-12-[(R)-2-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-ethyl]-27-methyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0^4,9]octacosane-2,3,10,20-tetraone

There total 12 articles about (1R,9S,12S,14S,24R,27R)-1,14-Dihydroxy-12-[(R)-2-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-ethyl]-27-methyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0^4,9]octacosane-2,3,10,20-tetraone 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:

(2R,3S)-1-[(1S,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-2-methyl-hex-5-en-3-ol (131719-87-4) → (1R,9S,12S,14S,24R,27R)-1,14-Dihydroxy-12-[(R)-2-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-ethyl]-27-methyl-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacosane-2,3,10,20-tetraone (137299-02-6)

Guidance literature:

Multi-step reaction with 12 steps

1: 1) t-BuOOH, 2) DIPEA / 1) V(O)acac2 / 1) CH₂Cl₂, 2) CH₂Cl₂

2: CuCN / diethyl ether / -40 - -20 °C

3: 2,6-lutidine / CH₂Cl₂

5: diethyl ether

6: H₂ / Pd(OH)2/C / ethyl acetate

7: t-BuLi / tetrahydrofuran / -40 °C

8: 65 percent / DIPEA, LiCl / acetonitrile / 20 h

9: 80 percent / H₂ / Pd(OH)2/C / ethyl acetate

10: 43 percent / (1-ethyl-3-(3-dimethylamino)propylcarbodiimide / DMAP / CH₂Cl₂ / 20 h

11: 2percent aq. HF / acetonitrile

12: CF₃COOH / 0.17 h / 0 °C

With 2,6-dimethylpyridine; tert.-butylhydroperoxide; hydrogen fluoride; hydrogen; tert.-butyl lithium; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium chloride; dmap; palladium dihydroxide; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4039(00)92266-4

Reference yield:

[(1R,2R,4S)-4-((2R,3S)-3-Benzyloxymethoxy-2-methyl-4-oxiranyl-butyl)-2-methoxy-cyclohexyloxy]-tert-butyl-dimethyl-silane (137298-96-5,137332-25-3) → (1R,9S,12S,14S,24R,27R)-1,14-Dihydroxy-12-[(R)-2-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-ethyl]-27-methyl-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacosane-2,3,10,20-tetraone (137299-02-6)

Guidance literature:

Multi-step reaction with 11 steps

1: CuCN / diethyl ether / -40 - -20 °C

2: 2,6-lutidine / CH₂Cl₂

4: diethyl ether

5: H₂ / Pd(OH)2/C / ethyl acetate

6: t-BuLi / tetrahydrofuran / -40 °C

7: 65 percent / DIPEA, LiCl / acetonitrile / 20 h

8: 80 percent / H₂ / Pd(OH)2/C / ethyl acetate

9: 43 percent / (1-ethyl-3-(3-dimethylamino)propylcarbodiimide / DMAP / CH₂Cl₂ / 20 h

10: 2percent aq. HF / acetonitrile

11: CF₃COOH / 0.17 h / 0 °C

With 2,6-dimethylpyridine; hydrogen fluoride; hydrogen; tert.-butyl lithium; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium chloride; dmap; palladium dihydroxide; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4039(00)92266-4

Reference yield:

(7S,9S,10R)-7-(tert-Butyl-dimethyl-silanyloxy)-11-[(1S,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-9-hydroxy-10-methyl-undecanoic acid methyl ester → (1R,9S,12S,14S,24R,27R)-1,14-Dihydroxy-12-[(R)-2-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-ethyl]-27-methyl-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacosane-2,3,10,20-tetraone (137299-02-6)

Guidance literature:

Multi-step reaction with 6 steps

1: t-BuLi / tetrahydrofuran / -40 °C

2: 65 percent / DIPEA, LiCl / acetonitrile / 20 h

3: 80 percent / H₂ / Pd(OH)2/C / ethyl acetate

4: 43 percent / (1-ethyl-3-(3-dimethylamino)propylcarbodiimide / DMAP / CH₂Cl₂ / 20 h

5: 2percent aq. HF / acetonitrile

6: CF₃COOH / 0.17 h / 0 °C

With hydrogen fluoride; hydrogen; tert.-butyl lithium; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium chloride; dmap; palladium dihydroxide; In tetrahydrofuran; dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4039(00)92266-4

upstream raw materials:

(2R,3S)-1-[(1S,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-2-methyl-hex-5-en-3-ol

[(1R,2R,4S)-4-((2R,3S)-3-Benzyloxymethoxy-2-methyl-4-oxiranyl-butyl)-2-methoxy-cyclohexyloxy]-tert-butyl-dimethyl-silane

((1S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-{(R)-2-[(1S,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-1-methyl-ethyl}-non-8-enyloxymethoxymethyl)-benzene

(7S,9S,10R)-9-Benzyloxymethoxy-7-(tert-butyl-dimethyl-silanyloxy)-11-[(1S,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-10-methyl-undecanoic acid methyl ester

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