Auristatin F

Base Information

• Chemical Name: Auristatin F
• CAS No.: 163768-50-1
• Molecular Formula: C40H67N5O8
• Molecular Weight: 746.001
• Mol file: 163768-50-1.mol

Synonyms:CS-1370;Auristatin F;Auristantin F;Auristatin F （AF）;Auristatin F TFA Salt;L-Phenylalanine, N,N-dimethyl-L-valyl-L-valyl-(3R,4S,5S)-3-methoxy-5-methyl-4-(methylamino)heptanoyl-(αR,βR,2S)-β-methoxy-α-methyl-2-pyrrolidinepropanoyl-;N,N-Dimethyl-L-valyl-N-[(3R,4S,5S)-1-{(2S)-2-[(1R,2R)-3-{[(1S)-1-carboxy-2-phenylethyl]amino}-1-methoxy-2-methyl-3-oxopropyl]-1-pyrrolidinyl}-3-methoxy-5-methyl-1-oxo-4-heptanyl]-N-methyl-L-valinamide;(S)-2-((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-2-((S)-2-(Dimethylamino)-3-methylbutanamido)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoic acid

Chemical Property of Auristatin F

Chemical Property:

• Boiling Point: 894.4±65.0 °C(Predicted)
• PKA: 3.56±0.10(Predicted)
• Density: 1.112±0.06 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)

Purity/Quality:

99% ^*data from raw suppliers

AuristatinFTFASalt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Auristatin F is a cytotoxin that works as a microtubule inhibitor and vascular damaging agent.
• Uses: Auristatin F is an antimitotic auristatin derivative that has been shown as a potent antitumor agent.

Technology Process of Auristatin F

There total 7 articles about Auristatin F 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:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (S)-2-((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-N,3-dimethyl-2-((S)-3-methyl-2-(methylamino)butanamido)butanamido)-3-methoxy-5-methylheptanoyl)-pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoic acid (745017-94-1) → ((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-2-((S)-2-(dimethylamino)-3-methylbutyrylamino)-N,3-dimethylbutyrylamino)-3-methoxy-5-methylheptanoyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropionyl)-L-phenylalanine (163768-50-1)

Guidance literature:

With sodium cyanoborohydride; acetic acid; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

Reference yield:

(S)-methyl 2-((2R,3R)-3-((S)-1-((6S,9S,12S,13R)-12-((S)-sec-butyl)-6,9-diisopropyl-13-methoxy-2,2,5,11-tetramethyl-4,7,10-trioxo-3-oxa-5,8,11-triazapentadecan-15-oyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoate (1415246-61-5) → ((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-2-((S)-2-(dimethylamino)-3-methylbutyrylamino)-N,3-dimethylbutyrylamino)-3-methoxy-5-methylheptanoyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropionyl)-L-phenylalanine (163768-50-1)

Guidance literature:

Multi-step reaction with 3 steps

1: water; lithium hydroxide / methanol / 2 h / 20 °C

2: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C

3: sodium cyanoborohydride; acetic acid / N,N-dimethyl-formamide / 2 h / 20 °C

With hydrogenchloride; water; sodium cyanoborohydride; acetic acid; lithium hydroxide; In 1,4-dioxane; methanol; N,N-dimethyl-formamide;

Reference yield:

(S)-methyl 2-((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-2-((tert-butoxycarbonyl)amino)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoyl)-pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoate (1415246-55-7) → ((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-2-((S)-2-(dimethylamino)-3-methylbutyrylamino)-N,3-dimethylbutyrylamino)-3-methoxy-5-methylheptanoyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropionyl)-L-phenylalanine (163768-50-1)

Guidance literature:

Multi-step reaction with 5 steps

1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C

2: 4-methyl-morpholine; HATU / N,N-dimethyl-formamide / 4 h / 20 °C

3: water; lithium hydroxide / methanol / 2 h / 20 °C

4: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C

5: sodium cyanoborohydride; acetic acid / N,N-dimethyl-formamide / 2 h / 20 °C

With 4-methyl-morpholine; hydrogenchloride; water; sodium cyanoborohydride; acetic acid; HATU; lithium hydroxide; In 1,4-dioxane; methanol; N,N-dimethyl-formamide;

upstream raw materials:

formaldehyd

(S)-2-((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-N,3-dimethyl-2-((S)-3-methyl-2-(methylamino)butanamido)butanamido)-3-methoxy-5-methylheptanoyl)-pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoic acid

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

(2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-2-((tert-butoxycarbonyl)amino)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanoic acid

Downstream raw materials:

C₂HF₃O₂*C₅₅H₉₆N₆O₁₃

C₄₄H₇₇N₇O₉

C₅₂H₇₉N₇O₁₁

Refernces

• 1、 -. "COMPOSITIONS CONTAINING, METHODS INVOLVING, AND USES OF NON-NATURAL AMINO ACID LINKED DOLASTATIN DERIVATIVES". Page/Page column 165. . Retrieved 2013/02/28.