dimethyl motuporine hydrate

Base Information

• Chemical Name: dimethyl motuporine hydrate
• CAS No.: 170872-85-2
• Molecular Formula: C₄₂H₆₃N₅O₁₁
• Molecular Weight: 813.989
• Mol file: 170872-85-2.mol

Synonyms:dimethyl motuporine hydrate

Chemical Property of dimethyl motuporine hydrate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl motuporine hydrate

There total 66 articles about dimethyl motuporine hydrate 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: 12.0%

2-[3-(2-{[4-(3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoylamino)-4-methoxycarbonyl-butyryl]-methyl-amino}-3-hydroxy-butyrylamino)-3-methoxycarbonyl-2-methyl-propionylamino]-3-methyl-butyric acid; compound with trifluoro-acetic acid → dimethyl motuporine hydrate (170872-85-2)

Guidance literature:

2-[3-(2-{[4-(3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoylamino)-4-methoxycarbonyl-butyryl]-methyl-amino}-3-hydroxy-butyrylamino)-3-methoxycarbonyl-2-methyl-propionylamino]-3-methyl-butyric acid; compound with trifluoro-acetic acid; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 0.0833333h;

2-[3-(2-{[4-(3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoylamino)-4-methoxycarbonyl-butyryl]-methyl-amino}-3-hydroxy-butyrylamino)-3-methoxycarbonyl-2-methyl-propionylamino]-3-methyl-butyric acid; compound with trifluoro-acetic acid; With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; at 0 - 20 ℃; for 19h; Further stages.;

DOI:10.1021/ja0206700

Reference yield:

N-(tert-butyloxycarbonyl)-γ-benzyl-D-glutamic acid (35793-73-8) → dimethyl motuporine hydrate (170872-85-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 100 percent / diethyl ether / 0 °C

2.1: 100 percent / H₂ / Pd/C / ethyl acetate / 1.5 h

3.1: 601 mg / BOP; DIPEA / CH₂Cl₂ / 44 h / 20 °C

4.1: TFA / CH₂Cl₂

5.1: 153 mg / HATU; collidine / dimethylformamide; CH₂Cl₂; toluene / 16 h / 0 - 20 °C

6.1: 95 percent / Zn; AcOH / 4 h / 20 °C

7.1: CH₂Cl₂ / 0.75 h / 20 °C

8.1: N-ethylmorpholine / CH₂Cl₂ / 0.08 h / 20 °C

8.2: 5.4 mg / HATU / CH₂Cl₂ / 24 h / 0 - 20 °C

With N-ethylmorpholine;; 2,3,5-trimethyl-pyridine; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; zinc; palladium on activated charcoal; In diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja0206700

Reference yield:

(E)-(4S, 5S)-methyl-4-azido-6-hydroxy-5-methyl-hex-2-enoate (194149-69-4) → dimethyl motuporine hydrate (170872-85-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 100 percent / imidazole / dimethylformamide / 0 - 20 °C

2.1: SnCl₂; MeOH / 6 h / 0 - 20 °C

3.1: aq. NaHCO₃ / dioxane / 14 h / 20 °C

4.1: O₃; pyridine / methanol / -78 °C

4.2: Me₂S / 4 h / 20 °C

5.1: 973 mg / CrCl₂ / tetrahydrofuran / 5 h / 20 °C

6.1: Cp₂Zr(H)Cl / tetrahydrofuran / 0.92 h / 20 - 50 °C

6.2: ZnCl₂ / tetrahydrofuran / 0.03 h / 20 °C

6.3: 84 percent / Pd(PPh₃)4 / 0.08 h / 20 °C

7.1: 100 percent / nBu₄NF / tetrahydrofuran / 1 h / 20 °C

8.1: 86 percent / PDC / dimethylformamide / 20 h / 20 °C

9.1: 16 mg / HATU; collidine / dimethylformamide; CH₂Cl₂; toluene / 16 h / 0 - 20 °C

10.1: 65 percent / TBAF*SiO₂ / tetrahydrofuran; dimethylformamide / 9 h / 20 °C

11.1: CH₂Cl₂ / 0.75 h / 20 °C

12.1: DIPEA / CH₂Cl₂ / 0.08 h / 20 °C

12.2: 12 percent / HATU / CH₂Cl₂ / 19 h / 0 - 20 °C

With pyridine; 1H-imidazole; chromium dichloride; 2,3,5-trimethyl-pyridine; methanol; dipyridinium dichromate; Schwartz's reagent; tetrabutyl ammonium fluoride; silica gel; sodium hydrogencarbonate; ozone; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; tin(ll) chloride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja0206700

upstream raw materials:

N-(tert-butyloxycarbonyl)-γ-benzyl-D-glutamic acid

(2R,3S)-3-methoxy-2-methyl-4-phenylbutanal

α-Methyl (2R)-N-(tert-butoxycarbonyl)glutamate ester

(2S,3S,4E,6E,8S,9S)-3-(tert-butoxycarbonyl)amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoic acid

Downstream raw materials:

(-)-motuporin