(5R,7S,(9E),10aR,11R,12R,13R,14aR)-11-benzyloxy-5,6,7,8,11,12,13,14-octahydro-8-hydroxy-4-(methoxymethoxy)-5,7,13-trimethyl-12,14a,3-(epoxymethino)-2H-1-benzoxacyclododecyn-2-2(4H,10aH)-one

Base Information

• Chemical Name: (5R,7S,(9E),10aR,11R,12R,13R,14aR)-11-benzyloxy-5,6,7,8,11,12,13,14-octahydro-8-hydroxy-4-(methoxymethoxy)-5,7,13-trimethyl-12,14a,3-(epoxymethino)-2H-1-benzoxacyclododecyn-2-2(4H,10aH)-one
• CAS No.: 1392307-74-2
• Molecular Formula: C₂₈H₃₆O₇
• Molecular Weight: 484.59

Synonyms:(5R,7S,(9E),10aR,11R,12R,13R,14aR)-11-benzyloxy-5,6,7,8,11,12,13,14-octahydro-8-hydroxy-4-(methoxymethoxy)-5,7,13-trimethyl-12,14a,3-(epoxymethino)-2H-1-benzoxacyclododecyn-2-2(4H,10aH)-one

Chemical Property of (5R,7S,(9E),10aR,11R,12R,13R,14aR)-11-benzyloxy-5,6,7,8,11,12,13,14-octahydro-8-hydroxy-4-(methoxymethoxy)-5,7,13-trimethyl-12,14a,3-(epoxymethino)-2H-1-benzoxacyclododecyn-2-2(4H,10aH)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of (5R,7S,(9E),10aR,11R,12R,13R,14aR)-11-benzyloxy-5,6,7,8,11,12,13,14-octahydro-8-hydroxy-4-(methoxymethoxy)-5,7,13-trimethyl-12,14a,3-(epoxymethino)-2H-1-benzoxacyclododecyn-2-2(4H,10aH)-one

There total 30 articles about (5R,7S,(9E),10aR,11R,12R,13R,14aR)-11-benzyloxy-5,6,7,8,11,12,13,14-octahydro-8-hydroxy-4-(methoxymethoxy)-5,7,13-trimethyl-12,14a,3-(epoxymethino)-2H-1-benzoxacyclododecyn-2-2(4H,10aH)-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: 96.0%

(5R,6R,7aR,8R,9R)-6-benzyloxy-6,7-dihydro-7-(E-2-iodovinyl)-3-[(2R,4S)-1-(methoxymethoxy)-2,4-dimethyl-5-oxopentyl]-9-methyl-5H-5,7a-ethano-2H-furo-[3.2-b]pyran-2-one → (5R,7S,(9E),10aR,11R,12R,13R,14aR)-11-benzyloxy-5,6,7,8,11,12,13,14-octahydro-8-hydroxy-4-(methoxymethoxy)-5,7,13-trimethyl-12,14a,3-(epoxymethino)-2H-1-benzoxacyclododecyn-2-2(4H,10aH)-one (1392307-74-2)

Guidance literature:

With chromium dichloride; nickel dichloride; In N,N-dimethyl-formamide; at 20 - 45 ℃; for 1.75h; Inert atmosphere;

DOI:10.1039/c3ob40692j

Reference yield: 90.0%

(5R,6R,7aR,7R,9R)-6-benzyloxy-6,7-dihydro-7-((E)-2-iodovinyl)-3-[(2R,4S)-1-(methoxymethoxy)-2,4-dimethyl-5-oxopentyl]-9-methyl-5H-5,7a-ethano-2H-furo-[3.2-b]pyran-2-one → (5R,7S,(9E),10aR,11R,12R,13R,14aR)-11-benzyloxy-5,6,7,8,11,12,13,14-octahydro-8-hydroxy-4-(methoxymethoxy)-5,7,13-trimethyl-12,14a,3-(epoxymethino)-2H-1-benzoxacyclododecyn-2-2(4H,10aH)-one (1392307-74-2)

Guidance literature:

With chromium dichloride; nickel dichloride; In N,N-dimethyl-formamide; at 20 - 45 ℃; for 1.75h; Inert atmosphere;

DOI:10.1002/anie.201108223

Reference yield:

(S)-4-benzyl-3-((2S,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-enoyl)oxazolidin-2-one → (5R,7S,(9E),10aR,11R,12R,13R,14aR)-11-benzyloxy-5,6,7,8,11,12,13,14-octahydro-8-hydroxy-4-(methoxymethoxy)-5,7,13-trimethyl-12,14a,3-(epoxymethino)-2H-1-benzoxacyclododecyn-2-2(4H,10aH)-one (1392307-74-2)

Guidance literature:

Multi-step reaction with 17 steps

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

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

3.1: dichloromethane / 20 h

4.1: diisobutylaluminium hydride / diethyl ether; toluene / -40 °C / Inert atmosphere

5.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / Cooling with ice

6.2: 0.25 h

7.1: pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 2 h / 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

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

10.2: -78 - 0 °C

10.3: 9 h / 60 °C

11.1: [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) / isopropyl alcohol / 2.5 h / 70 °C / Inert atmosphere

12.1: sodium isopropylate / isopropyl alcohol / 2 h / UV-irradiation

13.1: [2,2]bipyridinyl; tert.-butyl lithium / tetrahydrofuran; pentane / 0.75 h / -78 °C / Inert atmosphere

13.2: 0.83 h / -78 - -40 °C / Inert atmosphere

13.3: -40 - -25 °C / Inert atmosphere

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

14.2: 5 h / 20 °C

14.3: 48 h

15.1: chromium dichloride / tetrahydrofuran / 0.42 h / 20 - 50 °C / Inert atmosphere

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

17.1: 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; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); carbon tetrabromide; tert.-butyl lithium; sodium isopropylate; diisobutylaluminium hydride; Dess-Martin periodane; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; nickel dichloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; pentane; 2.1: Dess-Martin oxidation / 3.1: Wittig reaction / 7.1: Tsuji-Trost cyclization / 15.1: Takai olefination / 17.1: Nozaki-Hiyama-Kishi reaction;

DOI:10.1002/anie.201108223

upstream raw materials:

(2R,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexanecarbaldehyde

(2R,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-en-1-ol

(4R,5R,6R,(E))-ethyl 4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-6,10-dimethylundeca-2,9-dienoate

(4R,5R,6R,(E))-4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-6,10-dimethylundeca-2,9-dien-1-ol

Downstream raw materials:

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

(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

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

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

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