nordidemnin B

Base Information

• Chemical Name: nordidemnin B
• CAS No.: 117710-03-9
• Molecular Formula: C56H87 N7 O15
• Molecular Weight: 1098.35
• Mol file: 117710-03-9.mol

Synonyms:Didemnin A,N-[1-(2-hydroxy-1-oxopropyl)-L-prolyl]-3-[(3S,4R)-3-hydroxy-5-methyl-4-aminohexanoicacid]-, (S)-; 15H-Pyrrolo[2,1-f][1,15,4,7,10,20]dioxatetraazacyclotricosine,cyclic peptide deriv.; L-Tyrosine,(2S)-2-hydroxypropanoyl-L-prolyl-N-methyl-D-leucyl-L-threonyl-(3S,4R)-4-amino-3-hydroxy-5-methylhexanoyl-(2S,4S)-4-hydroxy-2,5-dimethyl-3-oxohexanoyl-L-leucyl-L-prolyl-N,O-dimethyl-,(9®4)-lactone

Chemical Property of nordidemnin B

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1271.4°Cat760mmHg
• Flash Point: 722.7°C
• PSA: 287.90000
• Density: 1.25g/cm³
• LogP: 2.78860

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of nordidemnin B

There total 16 articles about nordidemnin B 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: 57.0%

L-lactyl-L-prolyl-N-methyl-D-leucine (117710-19-7) + (5S,10S,14S,15R,18S,22S,24aS)-18-Amino-14-hydroxy-5-isobutyl-10,15-diisopropyl-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 (117733-99-0) → glycyltyrosine (117710-03-9)

Guidance literature:

With 4-methyl-morpholine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In dichloromethane; for 3h; Ambient temperature;

DOI:10.1021/jo00264a022

Reference yield:

Boc-D-Val-OH (22838-58-0) → glycyltyrosine (117710-03-9)

Guidance literature:

Multi-step reaction with 15 steps

1: 98 percent / triethylamine (TEA) / tetrahydrofuran / 2 h / 0 - 5 °C

2: lithium diisopropylamide / 1.) THF, hexane, from -78 deg C to -70 deg C, 15 min

3: NaBH₄ / CH₂Cl₂; acetic acid / 1 h / 0 - 5 °C

4: p-toluenesulfonic acid / 1.) reflux, 3 h, 2.) room temperature, overnight

5: 98 percent / 2 M NaOH / methanol / 0 - 5 °C

6: 92 percent / triethylamine (TEA), 4-(dimethylamino)pyridine (DMAP), isopropenyl chlorocarbonate (IPCC) / CH₂Cl₂ / 0.25 h / -5 °C

7: 100 percent / H₂ / 10percent Pd/C / propan-2-ol / 760 Torr

8: 97 percent / triethylamine (TEA) / tetrahydrofuran / 2 h / 0 - 5 °C

9: lithium diisopropylamide / 1.) THF, hexane, from -78 deg C to -70 deg C, 15 min

10: triethylamine (TEA), CuI / CH₂Cl₂ / 0.5 h / Ambient temperature

11: morpholine / tetrakis(triphenylphosphine)palladium / tetrahydrofuran / 0.17 h

12: 0.5 h

13: 54 percent / (1H-1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), NaHCO₃ / dimethylformamide / 24 h / Ambient temperature

14: 100 percent / H₂ / 10percent Pd/C / methanol / 2 h / 760 Torr / Ambient temperature

15: 57 percent / (1H-1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), N-methylmorpholine / CH₂Cl₂ / 3 h / Ambient temperature

With morpholine; 4-methyl-morpholine; dmap; sodium hydroxide; sodium tetrahydroborate; copper(l) iodide; Isopropenyl chloroformate; hydrogen; sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; toluene-4-sulfonic acid; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jo00264a022

Reference yield:

C49H71N5O14*C2HF3O2 (117710-29-9,117773-54-3) → glycyltyrosine (117710-03-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 54 percent / (1H-1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), NaHCO₃ / dimethylformamide / 24 h / Ambient temperature

2: 100 percent / H₂ / 10percent Pd/C / methanol / 2 h / 760 Torr / Ambient temperature

3: 57 percent / (1H-1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), N-methylmorpholine / CH₂Cl₂ / 3 h / Ambient temperature

With 4-methyl-morpholine; hydrogen; sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00264a022

upstream raw materials:

L-lactyl-L-prolyl-N-methyl-D-leucine

(5S,10S,14S,15R,18S,22S,24aS)-18-Amino-14-hydroxy-5-isobutyl-10,15-diisopropyl-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

Boc-D-Val-OH

C₄₉H₇₁N₅O₁₄*C₂HF₃O₂

Refernces