(4S,10S,13S,16S,19S,22R)-4,22-Dibenzyl-13-((S)-1-hydroxy-ethyl)-19-hydroxymethyl-16-isopropyl-17-thioxo-24-thia-3,6,12,15,18,21,26-heptaaza-tricyclo[21.2.1.0^6,10]hexacosa-1⁽²⁵⁾,23⁽²⁶⁾-diene-2,5,11,14,20-pentaone

Base Information

• Chemical Name: (4S,10S,13S,16S,19S,22R)-4,22-Dibenzyl-13-((S)-1-hydroxy-ethyl)-19-hydroxymethyl-16-isopropyl-17-thioxo-24-thia-3,6,12,15,18,21,26-heptaaza-tricyclo[21.2.1.0^6,10]hexacosa-1⁽²⁵⁾,23⁽²⁶⁾-diene-2,5,11,14,20-pentaone
• CAS No.: 170947-91-8
• Molecular Formula: C₃₈H₄₇N₇O₇S₂
• Molecular Weight: 777.966

Synonyms:(4S,10S,13S,16S,19S,22R)-4,22-Dibenzyl-13-((S)-1-hydroxy-ethyl)-19-hydroxymethyl-16-isopropyl-17-thioxo-24-thia-3,6,12,15,18,21,26-heptaaza-tricyclo[21.2.1.0^6,10]hexacosa-1⁽²⁵⁾,23⁽²⁶⁾-diene-2,5,11,14,20-pentaone

Chemical Property of (4S,10S,13S,16S,19S,22R)-4,22-Dibenzyl-13-((S)-1-hydroxy-ethyl)-19-hydroxymethyl-16-isopropyl-17-thioxo-24-thia-3,6,12,15,18,21,26-heptaaza-tricyclo[21.2.1.0^6,10]hexacosa-1⁽²⁵⁾,23⁽²⁶⁾-diene-2,5,11,14,20-pentaone

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Technology Process of (4S,10S,13S,16S,19S,22R)-4,22-Dibenzyl-13-((S)-1-hydroxy-ethyl)-19-hydroxymethyl-16-isopropyl-17-thioxo-24-thia-3,6,12,15,18,21,26-heptaaza-tricyclo[21.2.1.0^6,10]hexacosa-1⁽²⁵⁾,23⁽²⁶⁾-diene-2,5,11,14,20-pentaone

There total 7 articles about (4S,10S,13S,16S,19S,22R)-4,22-Dibenzyl-13-((S)-1-hydroxy-ethyl)-19-hydroxymethyl-16-isopropyl-17-thioxo-24-thia-3,6,12,15,18,21,26-heptaaza-tricyclo[21.2.1.0^6,10]hexacosa-1⁽²⁵⁾,23⁽²⁶⁾-diene-2,5,11,14,20-pentaone 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:

2-((R)-1-{(S)-2-[(S)-2-((2S,3S)-2-{[(S)-1-((S)-2-Amino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-hydroxy-butyrylamino)-3-methyl-thiobutyrylamino]-3-hydroxy-propionylamino}-2-phenyl-ethyl)-thiazole-4-carboxylic acid → (4S,10S,13S,16S,19S,22R)-4,22-Dibenzyl-13-((S)-1-hydroxy-ethyl)-19-hydroxymethyl-16-isopropyl-17-thioxo-24-thia-3,6,12,15,18,21,26-heptaaza-tricyclo[21.2.1.06,10]hexacosa-1(25),23(26)-diene-2,5,11,14,20-pentaone (170947-91-8)

Guidance literature:

With pentafluorophenyl diphenyl-phosphinate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 25 ℃; for 72h; Yield given;

DOI:10.1016/0040-4039(95)01166-F

Reference yield:

Phe-Pro-aThr-(S)-Val-Ψ(CS-NH)-(S)-Ser-(R)-Phe-Thz-OH*TFA → (4S,10S,13S,16S,19S,22R)-4,22-Dibenzyl-13-((S)-1-hydroxy-ethyl)-19-hydroxymethyl-16-isopropyl-17-thioxo-24-thia-3,6,12,15,18,21,26-heptaaza-tricyclo[21.2.1.06,10]hexacosa-1(25),23(26)-diene-2,5,11,14,20-pentaone (170947-91-8)

Guidance literature:

With 4-methyl-morpholine; diphenyl phosphoryl azide; In N,N-dimethyl-formamide; at 4 - 20 ℃; for 50h;

DOI:10.1039/a909360e

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanyl-L-proline (23420-32-8) → (4S,10S,13S,16S,19S,22R)-4,22-Dibenzyl-13-((S)-1-hydroxy-ethyl)-19-hydroxymethyl-16-isopropyl-17-thioxo-24-thia-3,6,12,15,18,21,26-heptaaza-tricyclo[21.2.1.06,10]hexacosa-1(25),23(26)-diene-2,5,11,14,20-pentaone (170947-91-8)

Guidance literature:

Multi-step reaction with 4 steps

1: Huenig's base; HOBt; DCC / dimethylformamide / 25.5 h / 0 - 25 °C

2: NaOH; H₂O / tetrahydrofuran; methanol / 1.5 h / 25 °C

3: CH₂Cl₂ / 4 h / 0 - 4 °C

4: N-methylmorpholine; diphenylphosphorazide / dimethylformamide / 50 h / 4 - 20 °C

With 4-methyl-morpholine; sodium hydroxide; diphenyl phosphoryl azide; water; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: Hydrolysis / 3: Substitution / 4: Acylation;

DOI:10.1039/a909360e

upstream raw materials:

N-tert-butoxycarbonyl-L-phenylalanyl-L-proline

Boc-aThr-(S)-Val-Ψ(CS-NH)-(S)-Ser-(R)-Phe-Thz-OMe

Boc-Phe-Pro-aThr-(S)-Val-Ψ(CS-NH)-(S)-Ser-(R)-Phe-Thz-OH

Boc-Phe-Pro-aThr-(S)-Val-Ψ(CS-NH)-(S)-Ser-(R)-Phe-Thz-OMe

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