tert-butyl N-[(2R)-1-[[(3S,6S,8S,12S,13R,16S,17R,20S,23S)-13-[(2S)-butan-2-yl]-12-hydroxy-20-[(4-methoxyphenyl)methyl]-6,17,21-trimethyl-3-(2-methylpropyl)-2,5,7,10,15,19,22-heptaoxo-8-propan-2-yl-9,18-dioxa-1,4,14,21-tetrazabicyclo[21.3.0]hexacosan-16-yl]amino]-4-methyl-1-oxopentan-2-yl]-N-methylcarbamate

Base Information

• Chemical Name: tert-butyl N-[(2R)-1-[[(3S,6S,8S,12S,13R,16S,17R,20S,23S)-13-[(2S)-butan-2-yl]-12-hydroxy-20-[(4-methoxyphenyl)methyl]-6,17,21-trimethyl-3-(2-methylpropyl)-2,5,7,10,15,19,22-heptaoxo-8-propan-2-yl-9,18-dioxa-1,4,14,21-tetrazabicyclo[21.3.0]hexacosan-16-yl]amino]-4-methyl-1-oxopentan-2-yl]-N-methylcarbamate
• CAS No.: 185461-51-2
• Molecular Formula: C₅₄H₈₆N₆O₁₄
• Molecular Weight: 1043.31
• Mol file: 185461-51-2.mol

Synonyms:

Chemical Property of tert-butyl N-[(2R)-1-[[(3S,6S,8S,12S,13R,16S,17R,20S,23S)-13-[(2S)-butan-2-yl]-12-hydroxy-20-[(4-methoxyphenyl)methyl]-6,17,21-trimethyl-3-(2-methylpropyl)-2,5,7,10,15,19,22-heptaoxo-8-propan-2-yl-9,18-dioxa-1,4,14,21-tetrazabicyclo[21.3.0]hexacosan-16-yl]amino]-4-methyl-1-oxopentan-2-yl]-N-methylcarbamate

Chemical Property:

• XLogP3: 7.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 15
• Exact Mass: 1042.62020144
• Heavy Atom Count: 74
• Complexity: 1950

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC(C)C1C(CC(=O)OC(C(=O)C(C(=O)NC(C(=O)N2CCCC2C(=O)N(C(C(=O)OC(C(C(=O)N1)NC(=O)C(CC(C)C)N(C)C(=O)OC(C)(C)C)C)CC3=CC=C(C=C3)OC)C)CC(C)C)C)C(C)C)O
• Isomeric SMILES: CC[C@H](C)[C@@H]1[C@H](CC(=O)O[C@H](C(=O)[C@@H](C(=O)N[C@H](C(=O)N2CCC[C@H]2C(=O)N([C@H](C(=O)O[C@@H]([C@@H](C(=O)N1)NC(=O)[C@@H](CC(C)C)N(C)C(=O)OC(C)(C)C)C)CC3=CC=C(C=C3)OC)C)CC(C)C)C)C(C)C)O

Technology Process of tert-butyl N-[(2R)-1-[[(3S,6S,8S,12S,13R,16S,17R,20S,23S)-13-[(2S)-butan-2-yl]-12-hydroxy-20-[(4-methoxyphenyl)methyl]-6,17,21-trimethyl-3-(2-methylpropyl)-2,5,7,10,15,19,22-heptaoxo-8-propan-2-yl-9,18-dioxa-1,4,14,21-tetrazabicyclo[21.3.0]hexacosan-16-yl]amino]-4-methyl-1-oxopentan-2-yl]-N-methylcarbamate

There total 13 articles about tert-butyl N-[(2R)-1-[[(3S,6S,8S,12S,13R,16S,17R,20S,23S)-13-[(2S)-butan-2-yl]-12-hydroxy-20-[(4-methoxyphenyl)methyl]-6,17,21-trimethyl-3-(2-methylpropyl)-2,5,7,10,15,19,22-heptaoxo-8-propan-2-yl-9,18-dioxa-1,4,14,21-tetrazabicyclo[21.3.0]hexacosan-16-yl]amino]-4-methyl-1-oxopentan-2-yl]-N-methylcarbamate 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:

Z-N,O-dimethyltyrosine-O-Boc-threonine-OSEM (126587-59-5) → Boc-didemnin A (185461-51-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 72 percent / aq. HF / acetonitrile / 7 h / -25 - -15 °C

2: 1-hydroxybenzotriazole, N-<(1H-benzotriazol-1-yl)(dimethylamino)methylene>-N-methylmethanaminium hexafluorophosphate N-oxide, N,N-diisopropylethylamine / tetrahydrofuran / 4 h / -10 - -5 °C

3: 99 percent / H₂ / Pd/C / tetrahydrofuran / 3 h / 760 Torr / Ambient temperature

4: 76 percent / N-<(dimethylamino)-1H-1,2,3-triazolo<4,5-b>pyridin-1-ylmethylene>-N-methylmethanaminium hexafluorophosphate N-oxide, 1-hydroxy-7-azabenzotriazole, N,N-diisopropylethylamine / tetrahydrofuran / 17 h / Ambient temperature

5: aq. HCl / dioxane / 1 h / Ambient temperature

6: 1-hydroxybenzotriazole, (1H-benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate, diisopropylethylamine / CH₂Cl₂ / 0.67 h / Ambient temperature

With hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; N-<(1H-benzotriazol-1-yl)(dimethylamino)methylene>-N-methylmethanaminium hexafluorophosphate N-oxide; N-<(dimethylamino)-1H-1,2,3-triazolo<4,5-b>pyridin-1-ylmethylene>-N-methylmethanaminium hexafluorophosphate N-oxide; hydrogen fluoride; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; acetonitrile;

DOI:10.1021/jo961932h

Reference yield:

(2S)-3-[4-(methyloxy)phenyl]-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)propanoic acid (118171-80-5) → Boc-didemnin A (185461-51-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 88 percent / DCC, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

2: 72 percent / aq. HF / acetonitrile / 7 h / -25 - -15 °C

3: 1-hydroxybenzotriazole, N-<(1H-benzotriazol-1-yl)(dimethylamino)methylene>-N-methylmethanaminium hexafluorophosphate N-oxide, N,N-diisopropylethylamine / tetrahydrofuran / 4 h / -10 - -5 °C

4: 99 percent / H₂ / Pd/C / tetrahydrofuran / 3 h / 760 Torr / Ambient temperature

5: 76 percent / N-<(dimethylamino)-1H-1,2,3-triazolo<4,5-b>pyridin-1-ylmethylene>-N-methylmethanaminium hexafluorophosphate N-oxide, 1-hydroxy-7-azabenzotriazole, N,N-diisopropylethylamine / tetrahydrofuran / 17 h / Ambient temperature

6: aq. HCl / dioxane / 1 h / Ambient temperature

7: 1-hydroxybenzotriazole, (1H-benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate, diisopropylethylamine / CH₂Cl₂ / 0.67 h / Ambient temperature

With hydrogenchloride; dmap; 1-hydroxy-7-aza-benzotriazole; N-<(1H-benzotriazol-1-yl)(dimethylamino)methylene>-N-methylmethanaminium hexafluorophosphate N-oxide; N-<(dimethylamino)-1H-1,2,3-triazolo<4,5-b>pyridin-1-ylmethylene>-N-methylmethanaminium hexafluorophosphate N-oxide; hydrogen fluoride; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; acetonitrile;

DOI:10.1021/jo961932h

Reference yield:

(S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,5-dimethyl-3-oxo-hexanoic acid benzyl ester (185515-75-7) → Boc-didemnin A (185461-51-2)

Guidance literature:

Multi-step reaction with 10 steps

1: H₂ / Pd/C / tetrahydrofuran / 2 h / 760 Torr / Ambient temperature

2: 1-hydroxybenzotriazole, N-<(1H-benzotriazol-1-yl)(dimethylamino)methylene>-N-methylmethanaminium hexafluorophosphate N-oxide, N,N-diisopropylethylamine / tetrahydrofuran / 1.) -5 deg C, 3 h, 2.) room temperature, 16 h

3: 97 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature

4: 84 percent / DCC, DMAP / CH₂Cl₂ / 1.) -10 - -5 deg C, 3 h, 2.) 4 deg C , 12 h

5: 105 mg / aq. HCl / dioxane / 3 h / Ambient temperature

6: 1-hydroxybenzotriazole, N-<(1H-benzotriazol-1-yl)(dimethylamino)methylene>-N-methylmethanaminium hexafluorophosphate N-oxide, N,N-diisopropylethylamine / tetrahydrofuran / 4 h / -10 - -5 °C

7: 99 percent / H₂ / Pd/C / tetrahydrofuran / 3 h / 760 Torr / Ambient temperature

8: 76 percent / N-<(dimethylamino)-1H-1,2,3-triazolo<4,5-b>pyridin-1-ylmethylene>-N-methylmethanaminium hexafluorophosphate N-oxide, 1-hydroxy-7-azabenzotriazole, N,N-diisopropylethylamine / tetrahydrofuran / 17 h / Ambient temperature

9: aq. HCl / dioxane / 1 h / Ambient temperature

10: 1-hydroxybenzotriazole, (1H-benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate, diisopropylethylamine / CH₂Cl₂ / 0.67 h / Ambient temperature

With hydrogenchloride; dmap; 1-hydroxy-7-aza-benzotriazole; N-<(1H-benzotriazol-1-yl)(dimethylamino)methylene>-N-methylmethanaminium hexafluorophosphate N-oxide; N-<(dimethylamino)-1H-1,2,3-triazolo<4,5-b>pyridin-1-ylmethylene>-N-methylmethanaminium hexafluorophosphate N-oxide; tetrabutyl ammonium fluoride; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1021/jo961932h

upstream raw materials:

N-tert-butoxycarbonyl-N-methyl-D-leucine

(5S,8S,10S,14S,15R,18S,19R,22S,24aS)-18-Amino-15-((S)-sec-butyl)-14-hydroxy-5-isobutyl-10-isopropyl-22-(4-methoxy-benzyl)-8,19,23-trimethyl-tetradecahydro-11,20-dioxa-3a,6,16,23-tetraaza-cyclopentacyclotricosene-4,7,9,12,17,21,24-heptaone

(2S)-3-[4-(methyloxy)phenyl]-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)propanoic acid

Z-N,O-dimethyltyrosine-O-Boc-threonine-OSEM

Downstream raw materials:

dehydrodidemnin B

Refernces