(2S,6R,E)-methyl 2-((benzyloxycarbonyl)(tert-butoxycarbonyl)amino)-6-hydroxy-4-methylhept-4-enoate

Base Information

Chemical Name:(2S,6R,E)-methyl 2-((benzyloxycarbonyl)(tert-butoxycarbonyl)amino)-6-hydroxy-4-methylhept-4-enoate
CAS No.:1354913-40-8
Molecular Formula:C₂₂H₃₁NO₇
Molecular Weight:421.491
Hs Code.:

Synonyms:(2S,6R,E)-methyl 2-((benzyloxycarbonyl)(tert-butoxycarbonyl)amino)-6-hydroxy-4-methylhept-4-enoate

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Chemical Property of (2S,6R,E)-methyl 2-((benzyloxycarbonyl)(tert-butoxycarbonyl)amino)-6-hydroxy-4-methylhept-4-enoate

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Technology Process of (2S,6R,E)-methyl 2-((benzyloxycarbonyl)(tert-butoxycarbonyl)amino)-6-hydroxy-4-methylhept-4-enoate

There total 7 articles about (2S,6R,E)-methyl 2-((benzyloxycarbonyl)(tert-butoxycarbonyl)amino)-6-hydroxy-4-methylhept-4-enoate 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: 86.0%

: 1354913-23-7
(2S,6R,E)-methyl 2-((benzyloxycarbonyl)(tert-butoxycarbonyl)amino)-6-(tert-butyldiphenylsilyloxy)-4-methylhept-4-enoate

: 1354913-40-8
(2S,6R,E)-methyl 2-((benzyloxycarbonyl)(tert-butoxycarbonyl)amino)-6-hydroxy-4-methylhept-4-enoate

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; acetonitrile; at 0 - 50 ℃; for 36h;
DOI:10.1039/c1ob06559a

Reference yield:

: 858132-44-2
(2E,4R)-4-([tert-butyl(diphenyl)silyl]oxy)-2-methylpent-2-en-1-ol

: 1354913-40-8
(2S,6R,E)-methyl 2-((benzyloxycarbonyl)(tert-butoxycarbonyl)amino)-6-hydroxy-4-methylhept-4-enoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; potassium carbonate / dichloromethane; water / 0.17 h / 20 °C

1.2: 5 h / 20 °C

2.1: N,N,N',N'-tetramethylguanidine / dichloromethane / 96 h / 0 - 20 °C

3.1: (+)-1,2-bis-[(2S,5S)-2,5-diethylphospholano]benzene (1,5-cycloctadiene)rhodium(I) trifluoromethanesulfonate; hydrogen / methanol / 21 h / 20 °C / 4500.45 Torr / Autoclave

4.1: dmap / tetrahydrofuran / 28 h / 50 °C

5.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran; acetonitrile / 36 h / 0 - 50 °C

With dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; (+)-1,2-bis-[(2S,5S)-2,5-diethylphospholano]benzene (1,5-cycloctadiene)rhodium(I) trifluoromethanesulfonate; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; hydrogen; sodium hydrogencarbonate; potassium carbonate; acetic acid; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; 2.1: Horner-Wadsworth-Emmons olefination;
DOI:10.1039/c1ob06559a

Reference yield:

: 858132-43-1
ethyl (2E,4R)-4-([tert-butyl(diphenyl)silyl]oxy)-2-methylpent-2-enoate

: 1354913-40-8
(2S,6R,E)-methyl 2-((benzyloxycarbonyl)(tert-butoxycarbonyl)amino)-6-hydroxy-4-methylhept-4-enoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C

2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; potassium carbonate / dichloromethane; water / 0.17 h / 20 °C

2.2: 5 h / 20 °C

3.1: N,N,N',N'-tetramethylguanidine / dichloromethane / 96 h / 0 - 20 °C

4.1: (+)-1,2-bis-[(2S,5S)-2,5-diethylphospholano]benzene (1,5-cycloctadiene)rhodium(I) trifluoromethanesulfonate; hydrogen / methanol / 21 h / 20 °C / 4500.45 Torr / Autoclave

5.1: dmap / tetrahydrofuran / 28 h / 50 °C

6.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran; acetonitrile / 36 h / 0 - 50 °C

With dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; (+)-1,2-bis-[(2S,5S)-2,5-diethylphospholano]benzene (1,5-cycloctadiene)rhodium(I) trifluoromethanesulfonate; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile; 3.1: Horner-Wadsworth-Emmons olefination;
DOI:10.1039/c1ob06559a