(1R*,9S*,16R*,17S*)-1,17-epoxy-16-methyl-8-phenoxycarbonyl-8-azatricyclo[7.7.1.0(2,7)]heptadeca-2⁽³⁾,4,6,12-tetraene-10.14-diyne

Base Information

• Chemical Name: (1R*,9S*,16R*,17S*)-1,17-epoxy-16-methyl-8-phenoxycarbonyl-8-azatricyclo[7.7.1.0(2,7)]heptadeca-2⁽³⁾,4,6,12-tetraene-10.14-diyne
• CAS No.: 291743-68-5
• Molecular Formula: C₂₄H₁₇NO₃
• Molecular Weight: 367.404

Synonyms:

Chemical Property of (1R*,9S*,16R*,17S*)-1,17-epoxy-16-methyl-8-phenoxycarbonyl-8-azatricyclo[7.7.1.0(2,7)]heptadeca-2⁽³⁾,4,6,12-tetraene-10.14-diyne

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Technology Process of (1R*,9S*,16R*,17S*)-1,17-epoxy-16-methyl-8-phenoxycarbonyl-8-azatricyclo[7.7.1.0(2,7)]heptadeca-2⁽³⁾,4,6,12-tetraene-10.14-diyne

There total 2 articles about (1R*,9S*,16R*,17S*)-1,17-epoxy-16-methyl-8-phenoxycarbonyl-8-azatricyclo[7.7.1.0(2,7)]heptadeca-2⁽³⁾,4,6,12-tetraene-10.14-diyne 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: 43.0%

C6H5O2CNC9H6(C2Co2(CO)6CHCHC2Co2(CO)6CHCH3)O → (1R*,9S*,16R*,17S*)-1,17-epoxy-16-methyl-8-phenoxycarbonyl-8-azatricyclo[7.7.1.0(2,7)]heptadeca-2(3),4,6,12-tetraene-10.14-diyne (291743-68-5) + C6H5O2CNC9H6(C2Co2(CO)6CHCHC2CHCH3)O

Guidance literature:

With sodium hydride; In tetrahydrofuran; under N2; NaH in mineral oil suspended in dry THF; cooled to 0°C;PhS(CH2)2OH added; soln. of Co complex in THF added; stirred at 0.degre e.C, then at room temp.;

DOI:10.1039/b307966j

Reference yield: 16.0%

(2S*,3S*,4R*)-3,4-epoxy-2-iodoethynyl-4-((R*)-[(3-iodo-1-methyl)prop-2-ynyl])-2H-quinoline-1-carboxylic acid phenyl ester (291743-74-3) + (Z)-bis(trimethylstannyl)ethylene (85263-63-4,98543-50-1,85271-55-2) → (1R*,9S*,16R*,17S*)-1,17-epoxy-16-methyl-8-phenoxycarbonyl-8-azatricyclo[7.7.1.0(2,7)]heptadeca-2(3),4,6,12-tetraene-10.14-diyne (291743-68-5) + C6H5O2CNC9H6(C2CHCHSn(CH3)3)(O)CH(CH3)C2CHCHSn(CH3)3 (650623-65-7)

Guidance literature:

With lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; under Ar, in the dark; bis(iodide) dissolved in DMF; Pd complex added; stirred at room temp. for 10 min; dry LiCl added; warmed to 70°C; soln. of Sn compd. in DMF added slowly over ca. 2 h; reacted for 15 min after addition; poured into crushed ice; extd. with Et2O; org. extracts washed with brine; dried (Na2SO4); filtered; solvent evapd. under reduced pressure; purified by chromy. (silica gel, petroleum ether-Et2O); elem. anal.;

DOI:10.1039/b307966j

Reference yield: 86.0%

dicobalt octacarbonyl (15226-74-1,61091-28-9,61117-58-6) + (1R*,9S*,16R*,17S*)-1,17-epoxy-16-methyl-8-phenoxycarbonyl-8-azatricyclo[7.7.1.0(2,7)]heptadeca-2(3),4,6,12-tetraene-10.14-diyne (291743-68-5) → C6H5O2CNC9H6(C2Co2(CO)6CHCHC2Co2(CO)6CHCH3)O

Guidance literature:

In dichloromethane; under N2; soln. of org. compd. in dry CH2Cl2 treated with Co2(CO)8; stirred at room temp. for 10 min; solvent evapd.; purified by chromy. (silica gel, petroleum ether-Et2O);

DOI:10.1039/b307966j

upstream raw materials:

(2S*,3S*,4R*)-3,4-epoxy-2-iodoethynyl-4-((R*)-[(3-iodo-1-methyl)prop-2-ynyl])-2H-quinoline-1-carboxylic acid phenyl ester

(Z)-bis(trimethylstannyl)ethylene

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