(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

Base Information

• Chemical Name: (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
• CAS No.: 1392307-62-8
• Molecular Formula: C₂₁H₂₆O₅
• Molecular Weight: 358.434

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

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Technology Process of (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

There total 20 articles about (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 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: 25.0%

ethyl 3-((1R,2S,3R,4R,5R)-3-(benzyloxy)-1,4-dihydroxy-5-methyl-2-vinylcyclohexyl)propiolate (1392307-60-6) → (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 (1392307-62-8) + C21H28O6 (1449483-67-3)

Guidance literature:

With (triphenylphosphine)gold(I)bis(trifluoromethanesulfonyl)imidate; In isopropyl alcohol; at 70 ℃; for 1.5h; Overall yield = 85 %;

DOI:10.1039/c3ob40692j

Reference yield: 21.0%

methanol (67-56-1) + ethyl 3-((1R,2S,3R,4R,5R)-3-(benzyloxy)-1,4-dihydroxy-5-methyl-2-vinylcyclohexyl)propiolate (1392307-60-6) → (5R,6S,7R,8R,9R)-7-(benzyloxy)-8-hydroxy-4-methoxy-9-methyl-6-vinyl-1-oxaspiro[4.5]dec-3-en-2-one (1392307-59-3) + (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 (1392307-62-8) + C22H30O6 + C21H28O6 (1449483-67-3)

Guidance literature:

With (triphenylphosphine)gold(I)bis(trifluoromethanesulfonyl)imidate; at 60 ℃; for 4h;

DOI:10.1039/c3ob40692j

Reference yield:

(S)-4-benzyl-3-((2S,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-enoyl)oxazolidin-2-one → (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 (1392307-62-8)

Guidance literature:

Multi-step reaction with 11 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

With pyrrolidine; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); carbon tetrabromide; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; isopropyl alcohol; toluene; 2.1: Dess-Martin oxidation / 3.1: Wittig reaction / 7.1: Tsuji-Trost cyclization;

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,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

(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

(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

(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

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