(4E,6E)-(2S,3S,8S,9S)-3-tert-Butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoic acid pentafluorophenyl ester

Base Information

Chemical Name:(4E,6E)-(2S,3S,8S,9S)-3-tert-Butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoic acid pentafluorophenyl ester
CAS No.:223923-73-7
Molecular Formula:C₃₁H₃₆F₅NO₅
Molecular Weight:597.623
Hs Code.:

Synonyms:(4E,6E)-(2S,3S,8S,9S)-3-tert-Butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoic acid pentafluorophenyl ester

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Chemical Property of (4E,6E)-(2S,3S,8S,9S)-3-tert-Butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoic acid pentafluorophenyl ester

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Technology Process of (4E,6E)-(2S,3S,8S,9S)-3-tert-Butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoic acid pentafluorophenyl ester

There total 10 articles about (4E,6E)-(2S,3S,8S,9S)-3-tert-Butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoic acid pentafluorophenyl ester 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: 88.0%

: 771-61-9
2,3,4,5,6-pentafluorophenol

: 134440-92-9
(2S,3S,4E,6E,8S,9S)-3-(tert-butoxycarbonyl)amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoic acid

: 223923-73-7
(4E,6E)-(2S,3S,8S,9S)-3-tert-Butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoic acid pentafluorophenyl ester

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 2h; Ambient temperature;
DOI:10.1021/jo982145i

Reference yield:

: 134440-96-3
(2S,3R)-N-tert-butoxycarbonyl-2-methyl-3-amino-4-hydroxy methyl butanoate

: 223923-73-7
(4E,6E)-(2S,3S,8S,9S)-3-tert-Butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoic acid pentafluorophenyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 123 mg / oxalyl chloride / CH₂Cl₂ / 1 h / -78 °C

2: 1.) n-BuLi / 1.) THF, -78 deg C (15 min), 0 deg C (30 min), 2.) THF, -> room temp., 20 h

3: 98 percent / aq. LiOH / tetrahydrofuran / 68 h / Ambient temperature

4: 88 percent / DCC, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

With dmap; lithium hydroxide; n-butyllithium; oxalyl dichloride; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo982145i

Reference yield:

: 134440-97-4
(2R,3S)-2-(tert-butoxycarbonyl)amino-3-methoxycarbonyl-3-methylbutanal

: 223923-73-7
(4E,6E)-(2S,3S,8S,9S)-3-tert-Butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoic acid pentafluorophenyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) n-BuLi / 1.) THF, -78 deg C (15 min), 0 deg C (30 min), 2.) THF, -> room temp., 20 h

2: 98 percent / aq. LiOH / tetrahydrofuran / 68 h / Ambient temperature

3: 88 percent / DCC, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

With dmap; lithium hydroxide; n-butyllithium; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo982145i