methyl (2S,6S,12Z,13aS,14aR,16aS)-6-[(tert-butoxycarbonyl)amino]-2-hydroxy-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate

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Chemical Name:methyl (2S,6S,12Z,13aS,14aR,16aS)-6-[(tert-butoxycarbonyl)amino]-2-hydroxy-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate
CAS No.:300831-46-3
Molecular Formula:C₂₄H₃₇N₃O₇
Molecular Weight:479.574
Hs Code.:

methyl (2S,6S,12Z,13aS,14aR,16aS)-6-[(tert-butoxycarbonyl)amino]-2-hydroxy-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate

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Chemical Property of methyl (2S,6S,12Z,13aS,14aR,16aS)-6-[(tert-butoxycarbonyl)amino]-2-hydroxy-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate

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Technology Process of methyl (2S,6S,12Z,13aS,14aR,16aS)-6-[(tert-butoxycarbonyl)amino]-2-hydroxy-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate

There total 13 articles about methyl (2S,6S,12Z,13aS,14aR,16aS)-6-[(tert-butoxycarbonyl)amino]-2-hydroxy-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate 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: 89.0%

: 300831-45-2
(1R,2S)-1-{[(2S,4S)-1-((S)-2-tert-Butoxycarbonylamino-non-8-enoyl)-4-hydroxy-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid methyl ester

: 300831-46-3,1098186-06-1
methyl (2S,6S,12Z,13aS,14aR,16aS)-6-[(tert-butoxycarbonyl)amino]-2-hydroxy-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate

Guidance literature:: Hoveyda's catalyst; In dichloromethane; for 28h; Heating / reflux;

Reference yield: 43.0%

: methyl (1R,2S)-1-[((4S)-1-{(2S)-2-[(3,3-dimethylbutanoyl)amino]non-8-enoyl}-4-hydroxy-L-prolyl)amino]-2-vinylcyclopropanecarboxylate

: 300831-46-3,1098186-06-1
methyl (2S,6S,12Z,13aS,14aR,16aS)-6-[(tert-butoxycarbonyl)amino]-2-hydroxy-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate

Guidance literature:: [1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(O-isopropoxyphenylmethylene)ruthenium; In dichloromethane; at 40 ℃; for 4h;

Reference yield:

: 17206-61-0
hept-6-enal

: 300831-46-3,1098186-06-1
methyl (2S,6S,12Z,13aS,14aR,16aS)-6-[(tert-butoxycarbonyl)amino]-2-hydroxy-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 49 percent / pyridine / 18 h / 20 °C

2.1: H₂ / [(COD)Rh((S,S)-Et-DUPHOS)]OTf / ethanol / 18 h / 2327.17 Torr

3.1: DMAP / tetrahydrofuran / 3.5 h / Heating

3.2: 13.43 g / LiOH*H₂O / H₂O; tetrahydrofuran / 18 h / 20 °C

4.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium BF₄; diisopropylethylamine / CH₂Cl₂ / 20 °C

4.2: 5.88 g / CH₂Cl₂ / 5 h / 20 °C

5.1: 85 percent / RuCl₂[(PCy₃)(2-isopropoxybenzylidene)] / CH₂Cl₂ / 18 h / Heating

With dmap; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; (+)-1,2-bis-((2S,5S)-2,5-diethylphospholano)benzene(cyclooctadiene)rhodium(I) trifluoromethanesulfonate; In tetrahydrofuran; pyridine; ethanol; dichloromethane; 1.1: Perkin reaction;
DOI:10.1021/ol0489907