(3S,5R,7S,9E,10aR,11R,12R,13R,14aR)-4-chloro-11-(benzyloxy)-6,7,11,12,13,14-hexahydro-5,7,13-trimethyl-12,14a,3-(epoxymethyno)-2H-1-benzoxacyclododecin-2,8(5H,10aH)-dione

Base Information

• Chemical Name: (3S,5R,7S,9E,10aR,11R,12R,13R,14aR)-4-chloro-11-(benzyloxy)-6,7,11,12,13,14-hexahydro-5,7,13-trimethyl-12,14a,3-(epoxymethyno)-2H-1-benzoxacyclododecin-2,8(5H,10aH)-dione
• CAS No.: 1449483-73-1
• Molecular Formula: C₂₆H₂₉ClO₅
• Molecular Weight: 456.966

Synonyms:(3S,5R,7S,9E,10aR,11R,12R,13R,14aR)-4-chloro-11-(benzyloxy)-6,7,11,12,13,14-hexahydro-5,7,13-trimethyl-12,14a,3-(epoxymethyno)-2H-1-benzoxacyclododecin-2,8(5H,10aH)-dione

Chemical Property of (3S,5R,7S,9E,10aR,11R,12R,13R,14aR)-4-chloro-11-(benzyloxy)-6,7,11,12,13,14-hexahydro-5,7,13-trimethyl-12,14a,3-(epoxymethyno)-2H-1-benzoxacyclododecin-2,8(5H,10aH)-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5R,7S,9E,10aR,11R,12R,13R,14aR)-4-chloro-11-(benzyloxy)-6,7,11,12,13,14-hexahydro-5,7,13-trimethyl-12,14a,3-(epoxymethyno)-2H-1-benzoxacyclododecin-2,8(5H,10aH)-dione

There total 26 articles about (3S,5R,7S,9E,10aR,11R,12R,13R,14aR)-4-chloro-11-(benzyloxy)-6,7,11,12,13,14-hexahydro-5,7,13-trimethyl-12,14a,3-(epoxymethyno)-2H-1-benzoxacyclododecin-2,8(5H,10aH)-dione 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:

(S)-4-benzyl-3-((2S,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-enoyl)oxazolidin-2-one → (3S,5R,7S,9E,10aR,11R,12R,13R,14aR)-4-chloro-11-(benzyloxy)-6,7,11,12,13,14-hexahydro-5,7,13-trimethyl-12,14a,3-(epoxymethyno)-2H-1-benzoxacyclododecin-2,8(5H,10aH)-dione (1449483-73-1)

Guidance literature:

Multi-step reaction with 19 steps

1.1: sodium tetrahydroborate / water; tetrahydrofuran / 20 h / 0 - 20 °C

2.1: Dess-Martin periodane / dichloromethane / 2.5 h / 20 °C

2.2: 20 h / 20 °C

3.1: diisobutylaluminium hydride / toluene; diethyl ether / 0.25 h / -40 °C / Inert atmosphere

4.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 15 h / 0 °C / Inert atmosphere

5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / Cooling with ice

6.1: periodic acid dihydrate / diethyl ether / 0.25 h

7.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; pyrrolidine / tetrahydrofuran / 20 °C / Inert atmosphere

8.1: triethylamine / dichloromethane / 1 h / 50 °C / Inert atmosphere

9.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / 20 °C

9.2: 2 h / 20 °C

10.1: diisopropylamine; n-butyllithium / hexane; toluene / 0.5 h / -78 °C

10.2: 0.33 h / -78 - 0 °C

10.3: 9 h / 60 °C

11.1: (triphenylphosphine)gold(I)bis(trifluoromethanesulfonyl)imidate / isopropyl alcohol / 1.5 h / 70 °C

12.1: hexane / UV-irradiation

13.1: sodium hydride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

14.1: tert.-butyl lithium; [2,2]bipyridinyl / tetrahydrofuran; pentane / 0.75 h / -78 °C / Inert atmosphere

14.2: 0.83 h / -78 - -40 °C / Inert atmosphere

14.3: -40 - -25 °C / Inert atmosphere

15.1: ozone / dichloromethane / 0.2 h / -78 °C

15.2: 5 h / -78 - 20 °C

15.3: 24 h / 20 °C

16.1: chromium dichloride / tetrahydrofuran / 0.42 h / 20 - 50 °C / Inert atmosphere; Glovebox

17.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C

18.1: chromium dichloride; nickel dichloride / N,N-dimethyl-formamide / 1.75 h / 20 - 45 °C / Inert atmosphere

With pyrrolidine; chromium dichloride; [2,2]bipyridinyl; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; periodic acid dihydrate; carbon tetrabromide; (triphenylphosphine)gold(I)bis(trifluoromethanesulfonyl)imidate; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; ozone; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; nickel dichloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; pentane; 16.1: |Takai-Utimoto Olefination;

DOI:10.1039/c3ob40692j

Reference yield:

(4R,5R,6R,(E))-ethyl 4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-6,10-dimethylundeca-2,9-dienoate (1392307-51-5) → (3S,5R,7S,9E,10aR,11R,12R,13R,14aR)-4-chloro-11-(benzyloxy)-6,7,11,12,13,14-hexahydro-5,7,13-trimethyl-12,14a,3-(epoxymethyno)-2H-1-benzoxacyclododecin-2,8(5H,10aH)-dione (1449483-73-1)

Guidance literature:

Multi-step reaction with 17 steps

1.1: diisobutylaluminium hydride / toluene; diethyl ether / 0.25 h / -40 °C / Inert atmosphere

2.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 15 h / 0 °C / Inert atmosphere

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / Cooling with ice

4.1: periodic acid dihydrate / diethyl ether / 0.25 h

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; pyrrolidine / tetrahydrofuran / 20 °C / Inert atmosphere

6.1: triethylamine / dichloromethane / 1 h / 50 °C / Inert atmosphere

7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / 20 °C

7.2: 2 h / 20 °C

8.1: diisopropylamine; n-butyllithium / hexane; toluene / 0.5 h / -78 °C

8.2: 0.33 h / -78 - 0 °C

8.3: 9 h / 60 °C

9.1: (triphenylphosphine)gold(I)bis(trifluoromethanesulfonyl)imidate / isopropyl alcohol / 1.5 h / 70 °C

10.1: hexane / UV-irradiation

11.1: sodium hydride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

12.1: tert.-butyl lithium; [2,2]bipyridinyl / tetrahydrofuran; pentane / 0.75 h / -78 °C / Inert atmosphere

12.2: 0.83 h / -78 - -40 °C / Inert atmosphere

12.3: -40 - -25 °C / Inert atmosphere

13.1: ozone / dichloromethane / 0.2 h / -78 °C

13.2: 5 h / -78 - 20 °C

13.3: 24 h / 20 °C

14.1: chromium dichloride / tetrahydrofuran / 0.42 h / 20 - 50 °C / Inert atmosphere; Glovebox

15.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C

16.1: chromium dichloride; nickel dichloride / N,N-dimethyl-formamide / 1.75 h / 20 - 45 °C / Inert atmosphere

With pyrrolidine; chromium dichloride; [2,2]bipyridinyl; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; periodic acid dihydrate; carbon tetrabromide; (triphenylphosphine)gold(I)bis(trifluoromethanesulfonyl)imidate; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; ozone; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; nickel dichloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene; pentane; 14.1: |Takai-Utimoto Olefination;

DOI:10.1039/c3ob40692j

Reference yield:

(R)-(-)-2,6-dimethyl-5-heptenal (106-72-9,77787-60-1,118333-87-2,116127-07-2) → (3S,5R,7S,9E,10aR,11R,12R,13R,14aR)-4-chloro-11-(benzyloxy)-6,7,11,12,13,14-hexahydro-5,7,13-trimethyl-12,14a,3-(epoxymethyno)-2H-1-benzoxacyclododecin-2,8(5H,10aH)-dione (1449483-73-1)

Guidance literature:

Multi-step reaction with 21 steps

1.1: di-n-butylboryl trifluoromethanesulfonate; triethylamine / dichloromethane / 1.25 h / -78 - 0 °C / Inert atmosphere

1.2: 5.56 h / -78 - 0 °C / Inert atmosphere

1.3: 1 h / 0 °C / Inert atmosphere

2.1: 2,4,6-trimethyl-pyridine / dichloromethane / 0.25 h / 0 - 20 °C / Inert atmosphere

3.1: sodium tetrahydroborate / water; tetrahydrofuran / 20 h / 0 - 20 °C

4.1: Dess-Martin periodane / dichloromethane / 2.5 h / 20 °C

4.2: 20 h / 20 °C

5.1: diisobutylaluminium hydride / toluene; diethyl ether / 0.25 h / -40 °C / Inert atmosphere

6.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 15 h / 0 °C / Inert atmosphere

7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / Cooling with ice

8.1: periodic acid dihydrate / diethyl ether / 0.25 h

9.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; pyrrolidine / tetrahydrofuran / 20 °C / Inert atmosphere

10.1: triethylamine / dichloromethane / 1 h / 50 °C / Inert atmosphere

11.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / 20 °C

11.2: 2 h / 20 °C

12.1: diisopropylamine; n-butyllithium / hexane; toluene / 0.5 h / -78 °C

12.2: 0.33 h / -78 - 0 °C

12.3: 9 h / 60 °C

13.1: (triphenylphosphine)gold(I)bis(trifluoromethanesulfonyl)imidate / isopropyl alcohol / 1.5 h / 70 °C

14.1: hexane / UV-irradiation

15.1: sodium hydride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

16.1: tert.-butyl lithium; [2,2]bipyridinyl / tetrahydrofuran; pentane / 0.75 h / -78 °C / Inert atmosphere

16.2: 0.83 h / -78 - -40 °C / Inert atmosphere

16.3: -40 - -25 °C / Inert atmosphere

17.1: ozone / dichloromethane / 0.2 h / -78 °C

17.2: 5 h / -78 - 20 °C

17.3: 24 h / 20 °C

18.1: chromium dichloride / tetrahydrofuran / 0.42 h / 20 - 50 °C / Inert atmosphere; Glovebox

19.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C

20.1: chromium dichloride; nickel dichloride / N,N-dimethyl-formamide / 1.75 h / 20 - 45 °C / Inert atmosphere

With pyrrolidine; 2,4,6-trimethyl-pyridine; chromium dichloride; [2,2]bipyridinyl; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; periodic acid dihydrate; carbon tetrabromide; di-n-butylboryl trifluoromethanesulfonate; (triphenylphosphine)gold(I)bis(trifluoromethanesulfonyl)imidate; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; ozone; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; nickel dichloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; pentane; 18.1: |Takai-Utimoto Olefination;

DOI:10.1039/c3ob40692j

upstream raw materials:

ethyl 3-((1R,2S,3R,4R,5R)-3-(benzyloxy)-1,4-dihydroxy-5-methyl-2-vinylcyclohexyl)propiolate

(Z)-ethyl 2-((1R,4R,5S,6R,7R)-6-(benzyloxy)-4-hydroxy-7-methyl-5-vinyl-2-oxabicyclo[2.2.2]octan-3-ylidene)acetate

(E)-ethyl 2-((1R,4R,5S,6R,7R)-6-(benzyloxy)-4-hydroxy-7-methyl-5-vinyl-2-oxabicyclo[2.2.2]octan-3-ylidene)acetate

(5R,6R,7aR,8S,9R)-8-vinyl-6,7-dihydro-9-(benzyloxy)-6-methyl-5H-5,7a-ethano-2H-furo[3,2-b]pyran-2-one

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