(4S,7S,10R,17S,20S,23R)-10-Benzyl-20-sec-butyl-4,17-bis-((S)-1-hydroxy-ethyl)-7-isobutyl-23-methyl-12,25-dithia-3,6,9,16,19,22,27,28-octaaza-tricyclo[22.2.1.1^11,14]octacosa-1⁽²⁶⁾,11⁽²⁸⁾,13,24⁽²⁷⁾-tetraene-2,5,8,15,18,21-hexaone

Base Information

• Chemical Name: (4S,7S,10R,17S,20S,23R)-10-Benzyl-20-sec-butyl-4,17-bis-((S)-1-hydroxy-ethyl)-7-isobutyl-23-methyl-12,25-dithia-3,6,9,16,19,22,27,28-octaaza-tricyclo[22.2.1.1^11,14]octacosa-1⁽²⁶⁾,11⁽²⁸⁾,13,24⁽²⁷⁾-tetraene-2,5,8,15,18,21-hexaone
• CAS No.: 101924-78-1
• Molecular Formula: C₃₈H₅₂N₈O₈S₂
• Molecular Weight: 813.012

Synonyms:(4S,7S,10R,17S,20S,23R)-10-Benzyl-20-sec-butyl-4,17-bis-((S)-1-hydroxy-ethyl)-7-isobutyl-23-methyl-12,25-dithia-3,6,9,16,19,22,27,28-octaaza-tricyclo[22.2.1.1^11,14]octacosa-1⁽²⁶⁾,11⁽²⁸⁾,13,24⁽²⁷⁾-tetraene-2,5,8,15,18,21-hexaone

Chemical Property of (4S,7S,10R,17S,20S,23R)-10-Benzyl-20-sec-butyl-4,17-bis-((S)-1-hydroxy-ethyl)-7-isobutyl-23-methyl-12,25-dithia-3,6,9,16,19,22,27,28-octaaza-tricyclo[22.2.1.1^11,14]octacosa-1⁽²⁶⁾,11⁽²⁸⁾,13,24⁽²⁷⁾-tetraene-2,5,8,15,18,21-hexaone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,7S,10R,17S,20S,23R)-10-Benzyl-20-sec-butyl-4,17-bis-((S)-1-hydroxy-ethyl)-7-isobutyl-23-methyl-12,25-dithia-3,6,9,16,19,22,27,28-octaaza-tricyclo[22.2.1.1^11,14]octacosa-1⁽²⁶⁾,11⁽²⁸⁾,13,24⁽²⁷⁾-tetraene-2,5,8,15,18,21-hexaone

There total 17 articles about (4S,7S,10R,17S,20S,23R)-10-Benzyl-20-sec-butyl-4,17-bis-((S)-1-hydroxy-ethyl)-7-isobutyl-23-methyl-12,25-dithia-3,6,9,16,19,22,27,28-octaaza-tricyclo[22.2.1.1^11,14]octacosa-1⁽²⁶⁾,11⁽²⁸⁾,13,24⁽²⁷⁾-tetraene-2,5,8,15,18,21-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: 12.5%

2-[(R)-1-((S)-2-{(2S,3S)-2-[(2-{(R)-1-[(S)-2-((2S,3S)-2-Amino-3-hydroxy-butyrylamino)-4-methyl-pentanoylamino]-2-phenyl-ethyl}-thiazole-4-carbonyl)-amino]-3-hydroxy-butyrylamino}-3-methyl-pentanoylamino)-ethyl]-thiazole-4-carboxylic acid; hydrochloride (101924-77-0) → (4S,7S,10R,17S,20S,23R)-10-Benzyl-20-sec-butyl-4,17-bis-((S)-1-hydroxy-ethyl)-7-isobutyl-23-methyl-12,25-dithia-3,6,9,16,19,22,27,28-octaaza-tricyclo[22.2.1.111,14]octacosa-1(26),11(28),13,24(27)-tetraene-2,5,8,15,18,21-hexaone (101924-78-1)

Guidance literature:

With diphenyl phosphoryl azide; triethylamine; In N,N-dimethyl-formamide; 1.) 4 deg C, 70 h 2.) room temp., 46 h;

DOI:10.1016/S0040-4039(00)98890-7

Reference yield:

N-tert-butoxycarbonyl-L-leucine (13139-15-6,53296-34-7) → (4S,7S,10R,17S,20S,23R)-10-Benzyl-20-sec-butyl-4,17-bis-((S)-1-hydroxy-ethyl)-7-isobutyl-23-methyl-12,25-dithia-3,6,9,16,19,22,27,28-octaaza-tricyclo[22.2.1.111,14]octacosa-1(26),11(28),13,24(27)-tetraene-2,5,8,15,18,21-hexaone (101924-78-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 94 percent / diethyl phosphorocyanidate, Et₃N

2: 1.) TFA 2.) NaHCO₃

3: 87 percent / DEPC, Et₃N

4: 1N NaOH / dimethylformamide

5: 94 percent / DEPC, Et₃N

6: 1N NaOH / dimethylformamide / 3 h / 0 °C

7: 4N HCl / dioxane / 2 h / Ambient temperature

8: 12.5 percent / diphenyl phosphorazidate, Et₃N / dimethylformamide / 1.) 4 deg C, 70 h 2.) room temp., 46 h

With hydrogenchloride; sodium hydroxide; diethyl cyanophosphonate; diphenyl phosphoryl azide; sodium hydrogencarbonate; triethylamine; diethyl dicarbonate; trifluoroacetic acid; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)98890-7

Reference yield:

Boc-D-Phe-OH (18942-49-9) → (4S,7S,10R,17S,20S,23R)-10-Benzyl-20-sec-butyl-4,17-bis-((S)-1-hydroxy-ethyl)-7-isobutyl-23-methyl-12,25-dithia-3,6,9,16,19,22,27,28-octaaza-tricyclo[22.2.1.111,14]octacosa-1(26),11(28),13,24(27)-tetraene-2,5,8,15,18,21-hexaone (101924-78-1)

Guidance literature:

Multi-step reaction with 10 steps

2: 1.) TFA 2.) NaHCO₃

3: 94 percent / diethyl phosphorocyanidate, Et₃N

4: 1.) TFA 2.) NaHCO₃

5: 87 percent / DEPC, Et₃N

6: 1N NaOH / dimethylformamide

7: 94 percent / DEPC, Et₃N

8: 1N NaOH / dimethylformamide / 3 h / 0 °C

9: 4N HCl / dioxane / 2 h / Ambient temperature

10: 12.5 percent / diphenyl phosphorazidate, Et₃N / dimethylformamide / 1.) 4 deg C, 70 h 2.) room temp., 46 h

With hydrogenchloride; sodium hydroxide; diethyl cyanophosphonate; diphenyl phosphoryl azide; sodium hydrogencarbonate; triethylamine; diethyl dicarbonate; trifluoroacetic acid; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)98890-7

upstream raw materials:

2-[(R)-1-((S)-2-{(2S,3S)-2-[(2-{(R)-1-[(S)-2-((2S,3S)-2-Amino-3-hydroxy-butyrylamino)-4-methyl-pentanoylamino]-2-phenyl-ethyl}-thiazole-4-carbonyl)-amino]-3-hydroxy-butyrylamino}-3-methyl-pentanoylamino)-ethyl]-thiazole-4-carboxylic acid; hydrochloride

N-tert-butoxycarbonyl-L-leucine

Boc-D-Phe-OH

2-((R)-1-Amino-ethyl)-thiazole-4-carboxylic acid methyl ester

Downstream raw materials:

patellamide B

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