(2S,8S,11S,14R,17S,20S,23S,24R)-8,14-Dibenzyl-11,17-bis-hydroxymethyl-20-isopropyl-24-methyl-25-oxa-6,9,12,15,18,21,26-heptaaza-tricyclo[21.2.1.0^2,6]hexacos-1⁽²⁶⁾-ene-7,10,13,16,19,22-hexaone

Base Information

• Chemical Name: (2S,8S,11S,14R,17S,20S,23S,24R)-8,14-Dibenzyl-11,17-bis-hydroxymethyl-20-isopropyl-24-methyl-25-oxa-6,9,12,15,18,21,26-heptaaza-tricyclo[21.2.1.0^2,6]hexacos-1⁽²⁶⁾-ene-7,10,13,16,19,22-hexaone
• CAS No.: 184296-14-8
• Molecular Formula: C₃₈H₄₉N₇O₉
• Molecular Weight: 747.849

Synonyms:(2S,8S,11S,14R,17S,20S,23S,24R)-8,14-Dibenzyl-11,17-bis-hydroxymethyl-20-isopropyl-24-methyl-25-oxa-6,9,12,15,18,21,26-heptaaza-tricyclo[21.2.1.0^2,6]hexacos-1⁽²⁶⁾-ene-7,10,13,16,19,22-hexaone

Chemical Property of (2S,8S,11S,14R,17S,20S,23S,24R)-8,14-Dibenzyl-11,17-bis-hydroxymethyl-20-isopropyl-24-methyl-25-oxa-6,9,12,15,18,21,26-heptaaza-tricyclo[21.2.1.0^2,6]hexacos-1⁽²⁶⁾-ene-7,10,13,16,19,22-hexaone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (2S,8S,11S,14R,17S,20S,23S,24R)-8,14-Dibenzyl-11,17-bis-hydroxymethyl-20-isopropyl-24-methyl-25-oxa-6,9,12,15,18,21,26-heptaaza-tricyclo[21.2.1.0^2,6]hexacos-1⁽²⁶⁾-ene-7,10,13,16,19,22-hexaone

There total 26 articles about (2S,8S,11S,14R,17S,20S,23S,24R)-8,14-Dibenzyl-11,17-bis-hydroxymethyl-20-isopropyl-24-methyl-25-oxa-6,9,12,15,18,21,26-heptaaza-tricyclo[21.2.1.0^2,6]hexacos-1⁽²⁶⁾-ene-7,10,13,16,19,22-hexaone 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:

Cbz-D-Phe (2448-45-5) → (2S,8S,11S,14R,17S,20S,23S,24R)-8,14-Dibenzyl-11,17-bis-hydroxymethyl-20-isopropyl-24-methyl-25-oxa-6,9,12,15,18,21,26-heptaaza-tricyclo[21.2.1.02,6]hexacos-1(26)-ene-7,10,13,16,19,22-hexaone (184296-14-8)

Guidance literature:

Multi-step reaction with 15 steps

1: N-methylmorpholine / CH₂Cl₂ / 0.25 h / -15 °C

2: CH₂Cl₂ / 0 - 20 °C

3: imidazole / CH₂Cl₂

4: H₂ / Pd/C / methanol

5: CH₂Cl₂ / 0 - 20 °C

6: imidazole / CH₂Cl₂

7: H₂ / Pd/C / methanol / 2 h

8: CH₂Cl₂ / 1 h / -15 - 10 °C

9: 100 percent / aq. LiOH / tetrahydrofuran / 3 h / Ambient temperature

10: Et₃N, pentafluorophenyl diphenylphosphinate

11: 93 percent / Et₃N-SO₂NCOOMe / tetrahydrofuran / 2 h / 60 °C

12: 88 percent / H₂ / Pd(OH)2 / methanol / 10 h

13: aq. NaOH / tetrahydrofuran; methanol / 2 h / Ambient temperature

14: NaHCO₃, pentafluorophenyl diphenylphosphinate / dimethylformamide / 96 h / 40 °C

15: nBu₄NF / tetrahydrofuran / 0.25 h / 0 °C

With 4-methyl-morpholine; 1H-imidazole; lithium hydroxide; sodium hydroxide; Burgess Reagent; pentafluorophenyl diphenyl-phosphinate; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; triethylamine; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja962859f

Reference yield:

(2S,8S,11S,14R,17S,20S,23S,24R)-8,14-Dibenzyl-11,17-bis-(tert-butyl-dimethyl-silanyloxymethyl)-20-isopropyl-24-methyl-25-oxa-6,9,12,15,18,21,26-heptaaza-tricyclo[21.2.1.02,6]hexacos-1(26)-ene-7,10,13,16,19,22-hexaone → (2S,8S,11S,14R,17S,20S,23S,24R)-8,14-Dibenzyl-11,17-bis-hydroxymethyl-20-isopropyl-24-methyl-25-oxa-6,9,12,15,18,21,26-heptaaza-tricyclo[21.2.1.02,6]hexacos-1(26)-ene-7,10,13,16,19,22-hexaone (184296-14-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.25h; Yield given;

DOI:10.1021/ja962859f

Reference yield:

(S)-N-(benzyloxycarbonyl)valine (1149-26-4) → (2S,8S,11S,14R,17S,20S,23S,24R)-8,14-Dibenzyl-11,17-bis-hydroxymethyl-20-isopropyl-24-methyl-25-oxa-6,9,12,15,18,21,26-heptaaza-tricyclo[21.2.1.02,6]hexacos-1(26)-ene-7,10,13,16,19,22-hexaone (184296-14-8)

Guidance literature:

Multi-step reaction with 9 steps

1: N-methylmorpholine / CH₂Cl₂ / 0.25 h / -15 °C

2: CH₂Cl₂ / 1 h / -15 - 10 °C

3: 100 percent / aq. LiOH / tetrahydrofuran / 3 h / Ambient temperature

4: Et₃N, pentafluorophenyl diphenylphosphinate

5: 93 percent / Et₃N-SO₂NCOOMe / tetrahydrofuran / 2 h / 60 °C

6: 88 percent / H₂ / Pd(OH)2 / methanol / 10 h

7: aq. NaOH / tetrahydrofuran; methanol / 2 h / Ambient temperature

8: NaHCO₃, pentafluorophenyl diphenylphosphinate / dimethylformamide / 96 h / 40 °C

9: nBu₄NF / tetrahydrofuran / 0.25 h / 0 °C

With 4-methyl-morpholine; lithium hydroxide; sodium hydroxide; Burgess Reagent; pentafluorophenyl diphenyl-phosphinate; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja962859f

upstream raw materials:

(S)-N-(benzyloxycarbonyl)valine

N-Cbz-L-Phe

Z-D-Phe-Ser-OMe

Cbz-D-Phe

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