(E)-(3S,6R,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-16-((1R,2R,3R)-2,3-dihydroxy-1-methyl-3-phenyl-propyl)-3-isobutyl-6-methyl-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone

Base Information

Chemical Name:(E)-(3S,6R,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-16-((1R,2R,3R)-2,3-dihydroxy-1-methyl-3-phenyl-propyl)-3-isobutyl-6-methyl-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone
CAS No.:196794-26-0
Molecular Formula:C₃₅H₄₅ClN₂O₉
Molecular Weight:673.203
Hs Code.:

(E)-(3S,6R,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-16-((1R,2R,3R)-2,3-dihydroxy-1-methyl-3-phenyl-propyl)-3-isobutyl-6-methyl-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone

Synonyms:(E)-(3S,6R,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-16-((1R,2R,3R)-2,3-dihydroxy-1-methyl-3-phenyl-propyl)-3-isobutyl-6-methyl-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone

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Chemical Property of (E)-(3S,6R,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-16-((1R,2R,3R)-2,3-dihydroxy-1-methyl-3-phenyl-propyl)-3-isobutyl-6-methyl-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone

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Technology Process of (E)-(3S,6R,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-16-((1R,2R,3R)-2,3-dihydroxy-1-methyl-3-phenyl-propyl)-3-isobutyl-6-methyl-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone

There total 36 articles about (E)-(3S,6R,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-16-((1R,2R,3R)-2,3-dihydroxy-1-methyl-3-phenyl-propyl)-3-isobutyl-6-methyl-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone 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: 77.0%

: (E)-(5S,6R,7R,8R)-5-((S)-2-{(R)-3-[(R)-2-Amino-3-(3-chloro-4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoyloxy)-7,8-dihydroxy-6-methyl-8-phenyl-oct-2-enoic acid

: 196794-26-0
(E)-(3S,6R,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-16-((1R,2R,3R)-2,3-dihydroxy-1-methyl-3-phenyl-propyl)-3-isobutyl-6-methyl-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone

Guidance literature:: With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 1.5h;
DOI:10.1002/chem.200500282

Reference yield:

: 196794-47-5
benzyl (2S)-2-[(2R)-3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl) propionylamino]-2-methylpropionyloxy]-4-methylpentanoate

: 196794-26-0
(E)-(3S,6R,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-16-((1R,2R,3R)-2,3-dihydroxy-1-methyl-3-phenyl-propyl)-3-isobutyl-6-methyl-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone

Guidance literature:: Multi-step reaction with 4 steps

1: H₂ / Pd/C / ethyl acetate / 3 h / 760 Torr

2: 93 percent / DMAP; EDC; Et₃N / CH₂Cl₂ / 31 h / 0 - 20 °C

3: aq. TFA / CH₂Cl₂ / 0 - 20 °C

4: 77 percent / HATU; DIPEA / dimethylformamide / 1.5 h / 0 - 20 °C

With dmap; hydrogen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1002/chem.200500282

Reference yield:

: 436143-83-8
2-methyl-7-phenyl-6,8-dioxabicyclo[3.2.1]octan-3-ol

: 196794-26-0
(E)-(3S,6R,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-16-((1R,2R,3R)-2,3-dihydroxy-1-methyl-3-phenyl-propyl)-3-isobutyl-6-methyl-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone

Guidance literature:: Multi-step reaction with 9 steps

1: BF₃*Et₂O / CH₂Cl₂

2: 93 percent / p-toluenesulfonic acid / acetone / 12 h / 20 °C

3: iodomethane; calcium carbonate; H₂O / acetonitrile / 6 h / 70 - 75 °C

4: 990 mg / Huenig's base; lithium perchlorate / acetonitrile / 4 h

5: 100 percent / morpholine / tetrakis(triphenylphosphine)palladium / tetrahydrofuran / 4 h / 20 °C

6: 107 mg / triethylamine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 0.5 h / 0 - 20 °C

7: 81 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

8: trifluoroacetic acid / CH₂Cl₂ / 2 h / 0 °C

9: 287 mg / 2-hydroxypyridine / toluene / 20 °C

With morpholine; 2-hydroxypyridin; dmap; boron trifluoride diethyl etherate; water; lithium perchlorate; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; calcium carbonate; methyl iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; acetone; toluene; acetonitrile; 4: Horner-Emmons reaction;
DOI:10.1021/ol020001r