tert-butyl (5S,6R,2E)-5-[(2S)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propanoylamino]propanoyloxy]-4-methylpentanoyloxy]-6-methylocta-2,7-dienoate

Base Information

Chemical Name:tert-butyl (5S,6R,2E)-5-[(2S)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propanoylamino]propanoyloxy]-4-methylpentanoyloxy]-6-methylocta-2,7-dienoate
CAS No.:311342-00-4
Molecular Formula:C₃₇H₅₆N₂O₁₀
Molecular Weight:688.859
Hs Code.:

tert-butyl (5S,6R,2E)-5-[(2S)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propanoylamino]propanoyloxy]-4-methylpentanoyloxy]-6-methylocta-2,7-dienoate

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Chemical Property of tert-butyl (5S,6R,2E)-5-[(2S)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propanoylamino]propanoyloxy]-4-methylpentanoyloxy]-6-methylocta-2,7-dienoate

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Technology Process of tert-butyl (5S,6R,2E)-5-[(2S)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propanoylamino]propanoyloxy]-4-methylpentanoyloxy]-6-methylocta-2,7-dienoate

There total 11 articles about tert-butyl (5S,6R,2E)-5-[(2S)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propanoylamino]propanoyloxy]-4-methylpentanoyloxy]-6-methylocta-2,7-dienoate 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:

: 27784-76-5
tert-butyl diethylphosphonoacetate

: 311342-00-4
tert-butyl (5S,6R,2E)-5-[(2S)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propanoylamino]propanoyloxy]-4-methylpentanoyloxy]-6-methylocta-2,7-dienoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: DBU; LiCl / acetonitrile / 0.5 h / 20 °C

1.2: 89 percent / acetonitrile / 2 h / 20 °C

2.1: 69 percent / tetrabutylammonium fluoride; Amberlyst-15 / tetrahydrofuran / 4.5 h

3.1: 173 mg / DIEA; DMAP / tetrahydrofuran / 0.75 h

With dmap; amberlyst-15; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; acetonitrile; 1.1: Metallation / 1.2: Horner-Emmons reaction / 2.1: Elimination / 3.1: Substitution;
DOI:10.1021/jo000767+

Reference yield:

: 68856-96-2
N-(tert-butoxycarbonyl)-O-methyl-D-tyrosine

: 311342-00-4
tert-butyl (5S,6R,2E)-5-[(2S)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propanoylamino]propanoyloxy]-4-methylpentanoyloxy]-6-methylocta-2,7-dienoate

Guidance literature:: Multi-step reaction with 6 steps

1: DCC / 1,2-dimethoxy-ethane / 24 h / 0 - 20 °C

2: 5.5 g / Et₃N / 1,2-dimethoxy-ethane; H₂O / 2 h

3: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / 1,2-dimethoxy-ethane; CH₂Cl₂ / 24 h / 20 °C

4: 5.90 g / acetonitrile / 18 h / 20 °C

5: DIEA; DMAP / tetrahydrofuran / 0.5 h

6: 173 mg / DIEA; DMAP / tetrahydrofuran / 0.75 h

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; acetonitrile; 1: Esterification / 2: Esterification / 3: Esterification / 4: Substitution / 5: Esterification / 6: Substitution;
DOI:10.1021/jo000767+

Reference yield:

: 178977-38-3
3-[(2R)-(tert-butoxycarbonylamino)-3-(4-methoxyphenyl)propanoylamino]propanoic acid

: 311342-00-4
tert-butyl (5S,6R,2E)-5-[(2S)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propanoylamino]propanoyloxy]-4-methylpentanoyloxy]-6-methylocta-2,7-dienoate

Guidance literature:: Multi-step reaction with 4 steps

1: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / 1,2-dimethoxy-ethane; CH₂Cl₂ / 24 h / 20 °C

2: 5.90 g / acetonitrile / 18 h / 20 °C

3: DIEA; DMAP / tetrahydrofuran / 0.5 h

4: 173 mg / DIEA; DMAP / tetrahydrofuran / 0.75 h

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; acetonitrile; 1: Esterification / 2: Substitution / 3: Esterification / 4: Substitution;
DOI:10.1021/jo000767+