(1S,2R,4S,5S,9S,10R,13R,14S,15S,17R,19S,20R)-13-Ethyl-17-(4-methoxy-phenyl)-2,4,7,7,10,14,19,20-octamethyl-6,8,12,16,18-pentaoxa-tricyclo[13.3.1.1^5,9]icosan-11-one

Base Information

• Chemical Name: (1S,2R,4S,5S,9S,10R,13R,14S,15S,17R,19S,20R)-13-Ethyl-17-(4-methoxy-phenyl)-2,4,7,7,10,14,19,20-octamethyl-6,8,12,16,18-pentaoxa-tricyclo[13.3.1.1^5,9]icosan-11-one
• CAS No.: 186489-81-6
• Molecular Formula: C₃₂H₅₀O₇
• Molecular Weight: 546.745

Synonyms:(1S,2R,4S,5S,9S,10R,13R,14S,15S,17R,19S,20R)-13-Ethyl-17-(4-methoxy-phenyl)-2,4,7,7,10,14,19,20-octamethyl-6,8,12,16,18-pentaoxa-tricyclo[13.3.1.1^5,9]icosan-11-one

Chemical Property of (1S,2R,4S,5S,9S,10R,13R,14S,15S,17R,19S,20R)-13-Ethyl-17-(4-methoxy-phenyl)-2,4,7,7,10,14,19,20-octamethyl-6,8,12,16,18-pentaoxa-tricyclo[13.3.1.1^5,9]icosan-11-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,4S,5S,9S,10R,13R,14S,15S,17R,19S,20R)-13-Ethyl-17-(4-methoxy-phenyl)-2,4,7,7,10,14,19,20-octamethyl-6,8,12,16,18-pentaoxa-tricyclo[13.3.1.1^5,9]icosan-11-one

There total 4 articles about (1S,2R,4S,5S,9S,10R,13R,14S,15S,17R,19S,20R)-13-Ethyl-17-(4-methoxy-phenyl)-2,4,7,7,10,14,19,20-octamethyl-6,8,12,16,18-pentaoxa-tricyclo[13.3.1.1^5,9]icosan-11-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:

(R)-2-((4S,5R,6S)-6-((2S,4R)-4-((4S,5S,6R)-6-((2R,3R)-3-(tert-butyldimethylsilyloxy)pentan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)pentan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)propanoic acid (890016-81-6) → (1S,2R,4S,5S,9S,10R,13R,14S,15S,17R,19S,20R)-13-Ethyl-17-(4-methoxy-phenyl)-2,4,7,7,10,14,19,20-octamethyl-6,8,12,16,18-pentaoxa-tricyclo[13.3.1.15,9]icosan-11-one (186489-81-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / TBAF / tetrahydrofuran / 10 h / 65 °C

2: 1.) i-Pr₂NEt, 2,4,6-trichlorobenzoyl chloride, 2.) N,N-(dimethylamino)pyridine / 1.) C₆H₆, RT, 5 h, 2.) C₆H₆, 45 min

With dmap; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;

DOI:10.1021/ja9806128

Reference yield:

(4R)-4-benzyl-3-{(2R)-2-[(4S,5R,6R)-6-((1S,2R,3R)-3-{(2R,4S,5S,6R)-6-[(1R,2R)-2-(tert-butyldimethylsiloxy)-1-methylbutyl]-2-(p-methoxyphenyl)-5-methyl-m-dioxan-4-yl}-2-hydroxy-1-methylbutyl)-2,2,5-trimethyl-m-dioxan-4-yl]propionyl}-2-oxazolidinone..... (211187-32-5) → (1S,2R,4S,5S,9S,10R,13R,14S,15S,17R,19S,20R)-13-Ethyl-17-(4-methoxy-phenyl)-2,4,7,7,10,14,19,20-octamethyl-6,8,12,16,18-pentaoxa-tricyclo[13.3.1.15,9]icosan-11-one (186489-81-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) tributyltin hydride, AIBN, 2.) CSA / 1.) 110 deg C, 30 min, 2.) CH₂Cl₂, 12 h

2: 72 percent / 30percent aq. H₂O₂, 0.2 M aq. LiOH / tetrahydrofuran / a) 0 deg C, 1 h, b) RT, 4 h

3: 88 percent / TBAF / tetrahydrofuran / 10 h / 65 °C

4: 1.) i-Pr₂NEt, 2,4,6-trichlorobenzoyl chloride, 2.) N,N-(dimethylamino)pyridine / 1.) C₆H₆, RT, 5 h, 2.) C₆H₆, 45 min

With dmap; lithium hydroxide; 2,2'-azobis(isobutyronitrile); 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; tri-n-butyl-tin hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;

DOI:10.1021/ja9806128

Reference yield:

(R)-4-Benzyl-3-[(R)-2-((4S,5R,6S)-6-{(1S,3R)-3-[(2R,4S,5S,6R)-6-[(1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-butyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-1-methyl-butyl}-2,2,5-trimethyl-[1,3]dioxan-4-yl)-propionyl]-oxazolidin-2-one (186489-79-2) → (1S,2R,4S,5S,9S,10R,13R,14S,15S,17R,19S,20R)-13-Ethyl-17-(4-methoxy-phenyl)-2,4,7,7,10,14,19,20-octamethyl-6,8,12,16,18-pentaoxa-tricyclo[13.3.1.15,9]icosan-11-one (186489-81-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / 30percent aq. H₂O₂, 0.2 M aq. LiOH / tetrahydrofuran / a) 0 deg C, 1 h, b) RT, 4 h

2: 88 percent / TBAF / tetrahydrofuran / 10 h / 65 °C

3: 1.) i-Pr₂NEt, 2,4,6-trichlorobenzoyl chloride, 2.) N,N-(dimethylamino)pyridine / 1.) C₆H₆, RT, 5 h, 2.) C₆H₆, 45 min

With dmap; lithium hydroxide; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;

DOI:10.1021/ja9806128

upstream raw materials:

(R)-2-((4S,5R,6S)-6-((2S,4R)-4-((4S,5S,6R)-6-((2R,3R)-3-(tert-butyldimethylsilyloxy)pentan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)pentan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)propanoic acid

(R)-4-Benzyl-3-[(R)-2-((4S,5R,6S)-6-{(1S,3R)-3-[(2R,4S,5S,6R)-6-[(1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-butyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-1-methyl-butyl}-2,2,5-trimethyl-[1,3]dioxan-4-yl)-propionyl]-oxazolidin-2-one

C₄₈H₇₅NO₁₀Si

(4R)-4-benzyl-3-{(2R)-2-[(4S,5R,6R)-6-((1S,2R,3R)-3-{(2R,4S,5S,6R)-6-[(1R,2R)-2-(tert-butyldimethylsiloxy)-1-methylbutyl]-2-(p-methoxyphenyl)-5-methyl-m-dioxan-4-yl}-2-hydroxy-1-methylbutyl)-2,2,5-trimethyl-m-dioxan-4-yl]propionyl}-2-oxazolidinone.....

Downstream raw materials:

(3R,4S,5R,6S,7S,9R,11R,12S,13R,14R)-14-ethyl-4,6,12-trihydroxy-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione

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