(Z)-methyl 2-((4R,5S,6R,7R,8R)-6-(benzyloxy)-7-hydroxy-8-methyl-2-oxo-5-vinyl-1-oxaspiro[3.5]nonan-3-ylidene)acetate

Base Information

Chemical Name:(Z)-methyl 2-((4R,5S,6R,7R,8R)-6-(benzyloxy)-7-hydroxy-8-methyl-2-oxo-5-vinyl-1-oxaspiro[3.5]nonan-3-ylidene)acetate
CAS No.:1449483-58-2
Molecular Formula:C₂₁H₂₄O₆
Molecular Weight:372.418
Hs Code.:

Synonyms:(Z)-methyl 2-((4R,5S,6R,7R,8R)-6-(benzyloxy)-7-hydroxy-8-methyl-2-oxo-5-vinyl-1-oxaspiro[3.5]nonan-3-ylidene)acetate

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Chemical Property of (Z)-methyl 2-((4R,5S,6R,7R,8R)-6-(benzyloxy)-7-hydroxy-8-methyl-2-oxo-5-vinyl-1-oxaspiro[3.5]nonan-3-ylidene)acetate

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Technology Process of (Z)-methyl 2-((4R,5S,6R,7R,8R)-6-(benzyloxy)-7-hydroxy-8-methyl-2-oxo-5-vinyl-1-oxaspiro[3.5]nonan-3-ylidene)acetate

There total 19 articles about (Z)-methyl 2-((4R,5S,6R,7R,8R)-6-(benzyloxy)-7-hydroxy-8-methyl-2-oxo-5-vinyl-1-oxaspiro[3.5]nonan-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: 77.0%

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 1449483-56-0
(1R,2S,3R,4R,5R)-3-(benzyloxy)-1-ethynyl-5-methyl-2-vinylcyclohexane-1,4-diol

: 1449483-58-2
(Z)-methyl 2-((4R,5S,6R,7R,8R)-6-(benzyloxy)-7-hydroxy-8-methyl-2-oxo-5-vinyl-1-oxaspiro[3.5]nonan-3-ylidene)acetate

Guidance literature:: With dichloro bis(acetonitrile) palladium(II); at 55 ℃; for 0.5h;
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

: 1449483-58-2
(Z)-methyl 2-((4R,5S,6R,7R,8R)-6-(benzyloxy)-7-hydroxy-8-methyl-2-oxo-5-vinyl-1-oxaspiro[3.5]nonan-3-ylidene)acetate

Guidance literature:: Multi-step reaction with 13 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: dmap; triethylamine / dichloromethane / 20 °C

5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / -10 °C

6.1: periodic acid dihydrate / diethyl ether / 0.25 h

7.1: triphenylphosphine; pyrrolidine; palladium diacetate / dimethyl sulfoxide / 20 °C

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: n-butyllithium / hexane; tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere

10.2: 0.58 h / -78 - 20 °C / Inert atmosphere

11.1: potassium carbonate / methanol / 1 h / 20 °C

12.1: hydrogen fluoride / acetonitrile / 96 h / 50 °C

13.1: dichloro bis(acetonitrile) palladium(II) / 0.5 h / 55 °C

With pyrrolidine; dmap; dichloro bis(acetonitrile) palladium(II); sodium tetrahydroborate; n-butyllithium; periodic acid dihydrate; hydrogen fluoride; palladium diacetate; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; toluene; acetonitrile;
DOI:10.1039/c3ob40692j

Reference yield:

: 1392307-50-4
(2R,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-en-1-ol

: 1449483-58-2
(Z)-methyl 2-((4R,5S,6R,7R,8R)-6-(benzyloxy)-7-hydroxy-8-methyl-2-oxo-5-vinyl-1-oxaspiro[3.5]nonan-3-ylidene)acetate

Guidance literature:: Multi-step reaction with 12 steps

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

1.2: 20 h / 20 °C

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

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

4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / Cooling with ice

5.1: periodic acid dihydrate / diethyl ether / 0.25 h

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

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

8.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / 20 °C

8.2: 2 h / 20 °C

9.1: n-butyllithium / hexane; tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere

9.2: 0.58 h / -78 - 20 °C / Inert atmosphere

10.1: potassium carbonate / methanol / 1 h / 20 °C

11.1: hydrogen fluoride / acetonitrile / 96 h / 50 °C

12.1: dichloro bis(acetonitrile) palladium(II) / 0.5 h / 55 °C

With pyrrolidine; dichloro bis(acetonitrile) palladium(II); tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; periodic acid dihydrate; carbon tetrabromide; hydrogen fluoride; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; acetonitrile;
DOI:10.1039/c3ob40692j