(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

Base Information

• Chemical Name: (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
• CAS No.: 120286-04-6
• Molecular Formula: C₄₂H₆₅N₅O₁₁
• Molecular Weight: 816.005
• Mol file: 120286-04-6.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 14 articles about (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 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:

(2S)-3-[4-(methyloxy)phenyl]-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)propanoic acid (118171-80-5) → (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 (120286-04-6)

Guidance literature:

Multi-step reaction with 6 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

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; 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:

Z-N,O-dimethyltyrosine-O-Boc-threonine-OSEM (126587-59-5) → (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 (120286-04-6)

Guidance literature:

Multi-step reaction with 5 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

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; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; 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) → (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 (120286-04-6)

Guidance literature:

Multi-step reaction with 9 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

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; 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:

C₅₀H₇₁N₅O₁₃

C₄₇H₇₃N₅O₁₃

(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

didemnin B

N-(Z-L-Pro)didemnin A

Cyclo<(N-L-prolyl-N-methyl-D-leucyl)-O-<oxy>-3-oxo-2,5-dimethylhexanoyl>-L-leucyl>-L-prolyl-N,O-dimethyl-L-tyrosyl>-L-threonyl>

Refernces

• 1、 Schmidt,Kroner,Griesser. "Total synthesis of the didemnins. 2. Synthesis of didemnin A, B, C and prolyldidemnin A". . p. 4407 - 4408. Retrieved 2007/10/02.