Mmad

Base Information

Chemical Name:Mmad
CAS No.:203849-91-6
Molecular Formula:C41H66N6O6S
Molecular Weight:771.06
Hs Code.:
UNII:W4ZIA40FZ9
DSSTox Substance ID:DTXSID101010182
Wikidata:Q81983573
Metabolomics Workbench ID:143723
ChEMBL ID:CHEMBL3359823
Mol file:203849-91-6.mol

Synonyms:MMAD;203849-91-6;Monomethylauristatin D;Monomethyl Dolastatin 10;Demethyldolastatin 10;(S)-N-((3R,4S,5S)-3-methoxy-1-((S)-2-((1R,2R)-1-methoxy-2-methyl-3-oxo-3-(((S)-2-phenyl-1-(thiazol-2-yl)ethyl)amino)propyl)pyrrolidin-1-yl)-5-methyl-1-oxoheptan-4-yl)-N,3-dimethyl-2-((S)-3-methyl-2-(methylamino)butanamido)butanamide;(2S)-N-[(2S)-1-[[(3R,4S,5S)-3-methoxy-1-[(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-[[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino]propyl]pyrrolidin-1-yl]-5-methyl-1-oxoheptan-4-yl]-methylamino]-3-methyl-1-oxobutan-2-yl]-3-methyl-2-(methylamino)butanamide;L-Valinamide, N-methyl-L-valyl-N-[(1S,2R)-2-methoxy-4-[(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-[[(1S)-2-phenyl-1-(2-thiazolyl)ethyl]amino]propyl]-1-pyrrolidinyl]-1-[(1S)-1-methylpropyl]-4-oxobutyl]-N-methyl-;L-VALINAMIDE, N-METHYL-L-VALYL-N-((1S,2R)-2-METHOXY-4-((2S)-2-((1R,2R)-1-METHOXY-2-METHYL-3-OXO-3-(((1S)-2-PHENYL-1-(2-THIAZOLYL)ETHYL)AMINO)PROPYL)-1-PYRROLIDINYL)-1-((1S)-1-METHYLPROPYL)-4-OXOBUTYL)-N-METHYL-;W4ZIA40FZ9;MONOMETHYLDOLASTATIN 10;SCHEMBL1687441;CHEMBL3359823;DTXSID101010182;AMY30772;EX-A2650;AKOS032960443;CS-1613;BS-15896;HY-15581;S6765;D83666;A926322;N-METHYL-L-VALYL-N-((1S,2R)-2-METHOXY-4-((2S)-2-((1R,2R)-1-METHOXY-2-METHYL-3-OXO-3-(((1S)-2-PHENYL-1-(2-THIAZOLYL)ETHYL)AMINO)PROPYL)-1-PYRROLIDINYL)-1-((1S)-1-METHYLPROPYL)-4-OXOBUTYL)-N-METHYL-L-VALINAMIDE

Suppliers and Price of Mmad

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Usbiological
Monomethyl Auristatin D
1mg
$ 333.00

TRC
MonomethylAuristatinD(MMAD)
5mg
$ 320.00

DC Chemicals
MMAD >98%
250 mg
$ 1500.00

DC Chemicals
MMAD >98%
1 g
$ 3200.00

Crysdot
MMAD 98+%
10mg
$ 364.00

Crysdot
MMAD 98+%
50mg
$ 875.00

Crysdot
MMAD 98+%
100mg
$ 1365.00

Crysdot
MMAD 98+%
5mg
$ 245.00

ChemScene
MMAD 99.86%
10mg
$ 140.00

ChemScene
MMAD 99.86%
5mg
$ 80.00

Total 39 raw suppliers

Chemical Property of Mmad

Chemical Property:

Boiling Point:906.1±65.0 °C(Predicted)
PKA:13.81±0.46(Predicted)
PSA：170.44000
Density:1.119±0.06 g/cm3(Predicted)
LogP:5.95880
Storage Temp.:Sealed in dry,Store in freezer, under -20°C
Solubility.:Soluble in DMSO
XLogP3:5.3
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:21
Exact Mass:770.47645502
Heavy Atom Count:54
Complexity:1190

Purity/Quality:

99%, ^*data from raw suppliers

Monomethyl Auristatin D ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:CCC(C)C(C(CC(=O)N1CCCC1C(C(C)C(=O)NC(CC2=CC=CC=C2)C3=NC=CS3)OC)OC)N(C)C(=O)C(C(C)C)NC(=O)C(C(C)C)NC
Isomeric SMILES:CC[C@H](C)[C@@H]([C@@H](CC(=O)N1CCC[C@H]1[C@@H]([C@@H](C)C(=O)N[C@@H](CC2=CC=CC=C2)C3=NC=CS3)OC)OC)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC
Description Monomethyl auristatin D (MMAD) is a potent tubulin inhibitor. Synonyms: Demethyldolastatin 10; Monomethylauristatin D; MMAD.
Uses MMAD is a tubulin inhibitor and used to produce site-specific antibody drug conjugates.

Technology Process of Mmad

There total 15 articles about Mmad 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:

: 69610-41-9,117625-90-8
Boc-L-Pro-H

: 203849-91-6
N-Me-Val-Val-Dil-Dap-Doe

Guidance literature:: Multi-step reaction with 7 steps

1: 18 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

2: 41 percent / BF₃*OEt₂ / CH₂Cl₂

3: H₂ / 5percent Pd/C / 2-methyl-propan-2-ol; H₂O

4: benzotriazolyloxytris(dimethylamino)phosphonium hexafluorophosphate, iso-Pr₂NEt / acetonitrile

5: HCl / dioxane / 1 h / Ambient temperature

6: 69 percent / diethyl phosphorocyanidate, Et₃N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h

7: TFA, thioanisole, m-cresol / 8 h / Ambient temperature

With hydrogenchloride; diethyl cyanophosphonate; methyl-phenyl-thioether; boron trifluoride diethyl etherate; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 3-methyl-phenol; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
DOI:10.1248/cpb.43.1706

Reference yield:

: 163768-51-2
benzyl (2R,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-hydroxy-2-methylpropanoate

: 203849-91-6
N-Me-Val-Val-Dil-Dap-Doe

Guidance literature:: Multi-step reaction with 6 steps

1: 41 percent / BF₃*OEt₂ / CH₂Cl₂

2: H₂ / 5percent Pd/C / 2-methyl-propan-2-ol; H₂O

3: benzotriazolyloxytris(dimethylamino)phosphonium hexafluorophosphate, iso-Pr₂NEt / acetonitrile

4: HCl / dioxane / 1 h / Ambient temperature

5: 69 percent / diethyl phosphorocyanidate, Et₃N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h

6: TFA, thioanisole, m-cresol / 8 h / Ambient temperature

With hydrogenchloride; diethyl cyanophosphonate; methyl-phenyl-thioether; boron trifluoride diethyl etherate; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 3-methyl-phenol; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
DOI:10.1248/cpb.43.1706

Reference yield:

: 135383-56-1
(3R,4S,5S)-4--3-methoxy-5-methylheptanoic acid

: 203849-91-6
N-Me-Val-Val-Dil-Dap-Doe

Guidance literature:: Multi-step reaction with 8 steps

1: H₂SO₄ / CH₂Cl₂

2: H₂ / 5percent Pd/C / 2-methyl-propan-2-ol; H₂O / 2 h

3: 1,3-dicyclohexylcarbodiimide / CH₂Cl₂

4: H₂ / 5percent Pd/C / 2-methyl-propan-2-ol; H₂O / 2 h

5: diethyl phosphorocyanidate, Et₃N / dimethylformamide / a) 0 deg C, 4 h, b) RT, 16 h

6: trifluoroacetic acid / CH₂Cl₂ / 1 h / Ambient temperature

7: 69 percent / diethyl phosphorocyanidate, Et₃N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h

8: TFA, thioanisole, m-cresol / 8 h / Ambient temperature

With diethyl cyanophosphonate; methyl-phenyl-thioether; sulfuric acid; hydrogen; 3-methyl-phenol; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1248/cpb.43.1706