(3S,6S,10S,11R,14R,15R,18S,21S)-14-[N-[2(S)-Hydroxypropionyl]-L-prolyl-D-(N-methyl)leucylamino]-10-hydroxy-3-isobutyl-6-isopropyl-18-(4-methoxybenzyl)-15,19-dimethyl-11-[1(S)-methylpropyl]-7,16-dioxa-1,4,12,19-tetraazabicyclo[19.3.0]tetracosane-2,5,8,13,1

Base Information

• Chemical Name: (3S,6S,10S,11R,14R,15R,18S,21S)-14-[N-[2(S)-Hydroxypropionyl]-L-prolyl-D-(N-methyl)leucylamino]-10-hydroxy-3-isobutyl-6-isopropyl-18-(4-methoxybenzyl)-15,19-dimethyl-11-[1(S)-methylpropyl]-7,16-dioxa-1,4,12,19-tetraazabicyclo[19.3.0]tetracosane-2,5,8,13,1
• CAS No.: 250211-78-0
• Molecular Formula: C₅₄H₈₅N₇O₁₄
• Molecular Weight: 1056.31

Synonyms:(-)-tamandarin A

Chemical Property of (3S,6S,10S,11R,14R,15R,18S,21S)-14-[N-[2(S)-Hydroxypropionyl]-L-prolyl-D-(N-methyl)leucylamino]-10-hydroxy-3-isobutyl-6-isopropyl-18-(4-methoxybenzyl)-15,19-dimethyl-11-[1(S)-methylpropyl]-7,16-dioxa-1,4,12,19-tetraazabicyclo[19.3.0]tetracosane-2,5,8,13,1

Chemical Property:

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Technology Process of (3S,6S,10S,11R,14R,15R,18S,21S)-14-[N-[2(S)-Hydroxypropionyl]-L-prolyl-D-(N-methyl)leucylamino]-10-hydroxy-3-isobutyl-6-isopropyl-18-(4-methoxybenzyl)-15,19-dimethyl-11-[1(S)-methylpropyl]-7,16-dioxa-1,4,12,19-tetraazabicyclo[19.3.0]tetracosane-2,5,8,13,1

There total 24 articles about (3S,6S,10S,11R,14R,15R,18S,21S)-14-[N-[2(S)-Hydroxypropionyl]-L-prolyl-D-(N-methyl)leucylamino]-10-hydroxy-3-isobutyl-6-isopropyl-18-(4-methoxybenzyl)-15,19-dimethyl-11-[1(S)-methylpropyl]-7,16-dioxa-1,4,12,19-tetraazabicyclo[19.3.0]tetracosane-2,5,8,13,1 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:

L-2-hydroxy-3-methylbutanoic acid allyl ester (178113-56-9) → (-)-tamandarin A (250211-78-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 0.5774 g / dicyclohexylcarbodiimide; 4-dimethylaminopyridine / toluene / 0 - 20 °C

2: morpholine / Pd(PPh₃)4 / tetrahydrofuran / 20 °C

3: 0.2315 g / EDAC*HCl; 4-dimethylaminopyridine / CH₂Cl₂ / 4.5 h / 0 - 20 °C

4: 96 percent / ethyldiisopropylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 - 20 °C

5: magnesium bromide diethyl etherate / CH₂Cl₂ / 6 h / 0 - 20 °C

6: H₂ / Pd/C / methanol; ethyl acetate / 5 h / 20 °C

7: 0.173 g / HATU; ethyldiisopropylamine / dimethylformamide / 0 - 20 °C

8: 127.5 mg / hydrogen chloride / ethyl acetate / -30 - 0 °C

9: 0.0471 g / BOP; N-methylmorpholine / CH₂Cl₂ / 0 - 20 °C

With morpholine; 4-methyl-morpholine; hydrogenchloride; dmap; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; magnesium bromide ethyl etherate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ol9910058

Reference yield:

(S)-2-Hydroxy-3-methylbutanoic acid (17407-55-5) → (-)-tamandarin A (250211-78-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 96 percent / anhydrous potassium carbonate; tetrabutylammonium iodide / dimethylformamide / 1 h / 20 °C

2: 0.5774 g / dicyclohexylcarbodiimide; 4-dimethylaminopyridine / toluene / 0 - 20 °C

3: morpholine / Pd(PPh₃)4 / tetrahydrofuran / 20 °C

4: 0.2315 g / EDAC*HCl; 4-dimethylaminopyridine / CH₂Cl₂ / 4.5 h / 0 - 20 °C

5: 96 percent / ethyldiisopropylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 - 20 °C

6: magnesium bromide diethyl etherate / CH₂Cl₂ / 6 h / 0 - 20 °C

7: H₂ / Pd/C / methanol; ethyl acetate / 5 h / 20 °C

8: 0.173 g / HATU; ethyldiisopropylamine / dimethylformamide / 0 - 20 °C

9: 127.5 mg / hydrogen chloride / ethyl acetate / -30 - 0 °C

10: 0.0471 g / BOP; N-methylmorpholine / CH₂Cl₂ / 0 - 20 °C

With morpholine; 4-methyl-morpholine; hydrogenchloride; dmap; hydrogen; tetra-(n-butyl)ammonium iodide; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; magnesium bromide ethyl etherate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ol9910058

Reference yield:

L-leucyl-L-prolyl-N,O-dimethyl-L-tyrosine-N-boc-O-SEM-L-threonine (250039-52-2) → (-)-tamandarin A (250211-78-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / ethyldiisopropylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 - 20 °C

2: magnesium bromide diethyl etherate / CH₂Cl₂ / 6 h / 0 - 20 °C

3: H₂ / Pd/C / methanol; ethyl acetate / 5 h / 20 °C

4: 0.173 g / HATU; ethyldiisopropylamine / dimethylformamide / 0 - 20 °C

5: 127.5 mg / hydrogen chloride / ethyl acetate / -30 - 0 °C

6: 0.0471 g / BOP; N-methylmorpholine / CH₂Cl₂ / 0 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; dmap; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; magnesium bromide ethyl etherate; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ol9910058

upstream raw materials:

L-lactyl-L-prolyl-N-methyl-D-leucine

(5S,8S,12S,13R,16S,17R,20S,22aS)-16-Amino-13-((S)-sec-butyl)-12-hydroxy-5-isobutyl-8-isopropyl-20-(4-methoxy-benzyl)-17,21-dimethyl-tetradecahydro-9,18-dioxa-3a,6,14,21-tetraaza-cyclopentacyclohenicosene-4,7,10,15,19,22-hexaone

C₅₃H₈₉N₅SiO₁₂

(S)-2-Hydroxy-3-methylbutanoic acid

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