(3S,6S,9S,12R,13R,14R,15R)-3-Benzyloxymethyl-12-ethyl-13-hydroxy-6-((R)-1-hydroxy-ethyl)-9-isopropyl-14-methyl-15-tridecyl-1-oxa-4,7,10-triaza-cyclopentadecane-2,5,8,11-tetraone

Base Information

Chemical Name:(3S,6S,9S,12R,13R,14R,15R)-3-Benzyloxymethyl-12-ethyl-13-hydroxy-6-((R)-1-hydroxy-ethyl)-9-isopropyl-14-methyl-15-tridecyl-1-oxa-4,7,10-triaza-cyclopentadecane-2,5,8,11-tetraone
CAS No.:867156-04-5
Molecular Formula:C₄₀H₆₇N₃O₈
Molecular Weight:717.987
Hs Code.:

(3S,6S,9S,12R,13R,14R,15R)-3-Benzyloxymethyl-12-ethyl-13-hydroxy-6-((R)-1-hydroxy-ethyl)-9-isopropyl-14-methyl-15-tridecyl-1-oxa-4,7,10-triaza-cyclopentadecane-2,5,8,11-tetraone

Synonyms:(3S,6S,9S,12R,13R,14R,15R)-3-Benzyloxymethyl-12-ethyl-13-hydroxy-6-((R)-1-hydroxy-ethyl)-9-isopropyl-14-methyl-15-tridecyl-1-oxa-4,7,10-triaza-cyclopentadecane-2,5,8,11-tetraone

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Chemical Property of (3S,6S,9S,12R,13R,14R,15R)-3-Benzyloxymethyl-12-ethyl-13-hydroxy-6-((R)-1-hydroxy-ethyl)-9-isopropyl-14-methyl-15-tridecyl-1-oxa-4,7,10-triaza-cyclopentadecane-2,5,8,11-tetraone

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Technology Process of (3S,6S,9S,12R,13R,14R,15R)-3-Benzyloxymethyl-12-ethyl-13-hydroxy-6-((R)-1-hydroxy-ethyl)-9-isopropyl-14-methyl-15-tridecyl-1-oxa-4,7,10-triaza-cyclopentadecane-2,5,8,11-tetraone

There total 11 articles about (3S,6S,9S,12R,13R,14R,15R)-3-Benzyloxymethyl-12-ethyl-13-hydroxy-6-((R)-1-hydroxy-ethyl)-9-isopropyl-14-methyl-15-tridecyl-1-oxa-4,7,10-triaza-cyclopentadecane-2,5,8,11-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:

: (2R,3R,4R,5R)-5-{(S)-2-[(2S,3R)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-3-benzyloxy-propionyloxy}-2-ethyl-3-hydroxy-4-methyl-octadecanoic acid; compound with trifluoro-acetic acid

: 867156-04-5
(3S,6S,9S,12R,13R,14R,15R)-3-Benzyloxymethyl-12-ethyl-13-hydroxy-6-((R)-1-hydroxy-ethyl)-9-isopropyl-14-methyl-15-tridecyl-1-oxa-4,7,10-triaza-cyclopentadecane-2,5,8,11-tetraone

Guidance literature:: With diethyl cyanophosphonate; triethylamine; In N,N-dimethyl-formamide; at 25 ℃;
DOI:10.1021/jo050628y

Reference yield:

: 867155-84-8
(2S,3R)-2-((4S,5S)-5-Ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-hexadecan-3-ol

: 867156-04-5
(3S,6S,9S,12R,13R,14R,15R)-3-Benzyloxymethyl-12-ethyl-13-hydroxy-6-((R)-1-hydroxy-ethyl)-9-isopropyl-14-methyl-15-tridecyl-1-oxa-4,7,10-triaza-cyclopentadecane-2,5,8,11-tetraone

Guidance literature:: Multi-step reaction with 8 steps

1.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1.5 h / 0 °C

1.2: 70 percent / 4-DMAP / tetrahydrofuran; toluene / 0 - 25 °C

2.1: H₂ / Pd/C-ethylenediamine complex / methanol / 0.5 h / 25 °C

3.1: 99 mg / HOBt; EDCI / dimethylformamide / 0.5 h / 25 °C

4.1: 81 percent / AcOH / tetrahydrofuran; H₂O / 18 h / 25 °C

5.1: TEMPO; KBr; NaClO / NaHCO₃ / CH₂Cl₂; H₂O / 1 h / 0 °C

6.1: 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 0.17 h / 25 °C

7.1: CH₂Cl₂ / 1 h / 0 °C

8.1: 22 mg / diethyl cyanophosphonate; triethylamine / dimethylformamide / 25 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; diethyl cyanophosphonate; 2,4,6-trichlorobenzoyl chloride; hydrogen; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; potassium bromide; palladium on activated charcoal; sodium hydrogencarbonate; ethylenediamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/jo050628y

Reference yield:

: 867155-80-4
(2S,3S,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-ethyl-4-methyl-octadecane-1,3-diol

: 867156-04-5
(3S,6S,9S,12R,13R,14R,15R)-3-Benzyloxymethyl-12-ethyl-13-hydroxy-6-((R)-1-hydroxy-ethyl)-9-isopropyl-14-methyl-15-tridecyl-1-oxa-4,7,10-triaza-cyclopentadecane-2,5,8,11-tetraone

Guidance literature:: Multi-step reaction with 10 steps

1.1: 93 percent / CSA / dimethylformamide / 0.5 h / 25 °C

2.1: 280 mg / TBAF / tetrahydrofuran / 96 h / 25 °C

3.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1.5 h / 0 °C

3.2: 70 percent / 4-DMAP / tetrahydrofuran; toluene / 0 - 25 °C

4.1: H₂ / Pd/C-ethylenediamine complex / methanol / 0.5 h / 25 °C

5.1: 99 mg / HOBt; EDCI / dimethylformamide / 0.5 h / 25 °C

6.1: 81 percent / AcOH / tetrahydrofuran; H₂O / 18 h / 25 °C

7.1: TEMPO; KBr; NaClO / NaHCO₃ / CH₂Cl₂; H₂O / 1 h / 0 °C

8.1: 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 0.17 h / 25 °C

9.1: CH₂Cl₂ / 1 h / 0 °C

10.1: 22 mg / diethyl cyanophosphonate; triethylamine / dimethylformamide / 25 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; diethyl cyanophosphonate; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; potassium bromide; palladium on activated charcoal; sodium hydrogencarbonate; ethylenediamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/jo050628y