Cyclo[L-alanyl-(2S,4E,6R,8S)-8-hydroxy-2,4,6-trimethyl-4-nonenoyl-L-alanyl-3-bromo-N-methyl-D-tyrosyl](9CI)

Base Information

Chemical Name:Cyclo[L-alanyl-(2S,4E,6R,8S)-8-hydroxy-2,4,6-trimethyl-4-nonenoyl-L-alanyl-3-bromo-N-methyl-D-tyrosyl](9CI)
CAS No.:108675-64-5
Molecular Formula:C28H40 Br N3 O6
Molecular Weight:594.546
Hs Code.:

Synonyms:L-Alanine,N-[3-bromo-N-[N-(8-hydroxy-2,4,6-trimethyl-1-oxo-4-nonenyl)-L-alanyl]-N-methyl-D-tyrosyl]-,p-lactone, [2S-(2R*,4E,6S*,8R*)]-;1-Oxa-4,7,10-triazacyclooctadecane, cyclic peptide deriv.; (+)-Geodiamolide B;Geodiamolide B; NSC 681481

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Chemical Property of Cyclo[L-alanyl-(2S,4E,6R,8S)-8-hydroxy-2,4,6-trimethyl-4-nonenoyl-L-alanyl-3-bromo-N-methyl-D-tyrosyl](9CI)

Chemical Property:

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MSDS Files:: SDS file from LookChem

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Technology Process of Cyclo[L-alanyl-(2S,4E,6R,8S)-8-hydroxy-2,4,6-trimethyl-4-nonenoyl-L-alanyl-3-bromo-N-methyl-D-tyrosyl](9CI)

There total 35 articles about Cyclo[L-alanyl-(2S,4E,6R,8S)-8-hydroxy-2,4,6-trimethyl-4-nonenoyl-L-alanyl-3-bromo-N-methyl-D-tyrosyl](9CI) 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%

: 119724-74-2
(E)-(3S,6R,9S,12S,16R,18S)-6-[3-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-benzyl]-3,7,9,12,14,16,18-heptamethyl-1-oxa-4,7,10-triaza-cyclooctadec-14-ene-2,5,8,11-tetraone

: 108675-64-5
(+)-geodiamolide B

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1016/S0040-4039(00)80460-8

Reference yield:

: 42406-77-9
L-tyrosine benzyl ester

: 108675-64-5
(+)-geodiamolide B

Guidance literature:: Multi-step reaction with 13 steps

1: 91.2 percent / Et₃N / dioxane; H₂O / 24 h / Ambient temperature

2: 93.3 percent / imidazole / dimethylformamide / 7 h / Ambient temperature

3: 82 percent / NaH / dimethylformamide / 3 h

4: 84.9 percent / TFA / CH₂Cl₂ / 4 h / 0 °C

5: 91 percent / Et₃N / CH₂Cl₂ / 10 h / Ambient temperature

6: 86.4 percent / H₂ / 10percent Pd-C / ethanol / 15 h

7: 82.8 percent / N-methylmorpholine, DCC, HOBT / CH₂Cl₂ / 5 h / 0 °C

8: 87 percent / Br₂ / CHCl₃ / 3 h / -5 °C

9: 77 percent / 2,6-lutidine, TBSOTf / CH₂Cl₂ / 2.5 h / Ambient temperature

10: 68 percent / HOBT, DCC / tetrahydrofuran / 5 h / 0 °C

11: 1.) ethanedithiol, 2.) trifluoroacetic acid / 1.) CH₂Cl₂, 0 deg C, 0.5 h, 2.) 0 deg C, 4 h

12: 1.) Et₃N, 2,4,6-trichlorobenzoyl chloride, 2.) DMAP / 1.) THF, RT, 2.5 h, 2.) benzene, reflux

13: 85 percent / n-Bu₄NF / tetrahydrofuran / 0.17 h / 0 °C

With 4-methyl-morpholine; 1H-imidazole; 2,6-dimethylpyridine; dmap; ethandithiol; 2,4,6-trichlorobenzoyl chloride; t-butyldimethylsiyl triflate; tetrabutyl ammonium fluoride; hydrogen; bromine; sodium hydride; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide;

Reference yield:

: 19391-35-6
N-tert-butoxycarbonyl-L-tyrosine benzyl ester

: 108675-64-5
(+)-geodiamolide B

Guidance literature:: Multi-step reaction with 12 steps

1: 93.3 percent / imidazole / dimethylformamide / 7 h / Ambient temperature

2: 82 percent / NaH / dimethylformamide / 3 h

3: 84.9 percent / TFA / CH₂Cl₂ / 4 h / 0 °C

4: 91 percent / Et₃N / CH₂Cl₂ / 10 h / Ambient temperature

5: 86.4 percent / H₂ / 10percent Pd-C / ethanol / 15 h

6: 82.8 percent / N-methylmorpholine, DCC, HOBT / CH₂Cl₂ / 5 h / 0 °C

7: 87 percent / Br₂ / CHCl₃ / 3 h / -5 °C

8: 77 percent / 2,6-lutidine, TBSOTf / CH₂Cl₂ / 2.5 h / Ambient temperature

9: 68 percent / HOBT, DCC / tetrahydrofuran / 5 h / 0 °C

10: 1.) ethanedithiol, 2.) trifluoroacetic acid / 1.) CH₂Cl₂, 0 deg C, 0.5 h, 2.) 0 deg C, 4 h

11: 1.) Et₃N, 2,4,6-trichlorobenzoyl chloride, 2.) DMAP / 1.) THF, RT, 2.5 h, 2.) benzene, reflux

12: 85 percent / n-Bu₄NF / tetrahydrofuran / 0.17 h / 0 °C

With 4-methyl-morpholine; 1H-imidazole; 2,6-dimethylpyridine; dmap; ethandithiol; 2,4,6-trichlorobenzoyl chloride; t-butyldimethylsiyl triflate; tetrabutyl ammonium fluoride; hydrogen; bromine; sodium hydride; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide;