Boc-D-methionine

Base Information

• Chemical Name: Boc-D-methionine
• CAS No.: 5241-66-7
• Molecular Formula: C10H19NO4S
• Molecular Weight: 249.331
• Hs Code.: 2930 90 98
• European Community (EC) Number: 226-043-7
• DSSTox Substance ID: DTXSID401285150
• Nikkaji Number: J269.482D
• Wikidata: Q106902940
• Mol file: 5241-66-7.mol

Synonyms:5241-66-7;Boc-D-Met-OH;Boc-D-methionine;N-Boc-D-methionine;N-(tert-Butoxycarbonyl)-D-methionine;N-(TERT-BUTYLOXYCARBONYL)-D-METHIONINE;N-tert-Butoxycarbonyl-D-methionine;EINECS 226-043-7;(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-methylsulfanylbutanoic acid;D-METHIONINE, N-[(1,1-DIMETHYLETHOXY)CARBONYL]-;(R)-2-((tert-Butoxycarbonyl)amino)-4-(methylthio)butanoic acid;MFCD00038256;D-Methionine, N-((1,1-dimethylethoxy)carbonyl)-;C10-H19-N-O4-S;boc-(d)-methionine;(R)-BOC-methionine;t-Boc-D-Met-OH;N-Boc-(D)-methionine;(TERT-BUTOXYCARBONYL)-D-METHIONINE;BOC-(D)-Met-OH;t-butoxycarbonyl-D-methionine;SCHEMBL1486229;N-t-butyloxycarbonyl D-methionine;DTXSID401285150;(2R)-2-(tert-butoxycarbonylamino)-4-methylsulfanyl-butanoic acid;(R)-N-(tert-butoxycarbonyl)methionine;AKOS016842875;AC-8628;AM81979;CS-W004098;HY-W004098;AC-19280;Boc-D-Met-OH, >=98.0% (TLC);DS-15161;B2967;EN300-154390;F10921;J-300195;Q-101593;N-alpha-t-Butyloxycarbonyl-D-methionine (Boc-D-Met-OH);(R)-2-TERT-BUTOXYCARBONYLAMINO-4-METHYLSULFANYL-BUTYRIC ACID;(2R)-2-[(TERT-BUTOXYCARBONYL)AMINO]-4-(METHYLTHIO)BUTANOIC ACID;(2R)-2-{[(tert-butoxy)carbonyl]amino}-4-(methylsulfanyl)butanoic acid;(R)-2-(TERT-BUTOXYCARBONYLAMINO)-4-(METHYLTHIO)BUTANOIC ACID

Chemical Property of Boc-D-methionine

Chemical Property:

• Appearance/Colour: white - off-white powder
• Vapor Pressure: 4.56E-08mmHg at 25°C
• Melting Point: 47-50 °C
• Refractive Index: 22 ° (C=1, MeOH)
• Boiling Point: 415.5 °C at 760 mmHg
• PKA: 3.83±0.10(Predicted)
• Flash Point: 205.1 °C
• PSA: 100.93000
• Density: 1.16 g/cm³
• LogP: 2.10830
• Storage Temp.: Store at RT.
• Solubility.: soluble in Methanol
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 249.10347926
• Heavy Atom Count: 16
• Complexity: 250

Purity/Quality:

98% ^*data from raw suppliers

Boc-D-methionine 99+% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CCSC)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CCSC)C(=O)O
• Uses: N-Boc-D-methionine is an N-Boc-protected form of D-Methionine (M260550). D-Methionine is an isomer of L-Methionine (M260440), and is known to be a cytoprotectant against Cisplatin (C499500), an anticancer agent. D-Methionine is also used to prevent noise- and drug-induced hearing loss, as well as hair loss (all of which may also be caused by Cisplatin or aminoglycosides).

Technology Process of Boc-D-methionine

There total 2 articles about Boc-D-methionine 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: 100.0%

D-methionine (348-67-4,26062-47-5,58576-49-1) + di-tert-butyl dicarbonate (24424-99-5) → (R)-N-(tert-butoxycarbonyl)methionine (5241-66-7)

Guidance literature:

With sodium carbonate; citric acid; In 1,4-dioxane; water;

Reference yield:

D-methionine (348-67-4,26062-47-5,58576-49-1) → (R)-N-(tert-butoxycarbonyl)methionine (5241-66-7)

Guidance literature:

DOI:10.1039/DT9840002305

Reference yield: 99.0%

(R)-N-(tert-butoxycarbonyl)methionine (5241-66-7) + [3-(benzyloxy)phenyl](3-chlorophenyl)methylamine (440105-55-5) → (3R)-2-[(tert-butoxycarbonyl)amino]-4-(methylmercapto)-N-{[3-(benzyloxy)phenyl](3-chlorophenyl)methyl}butyramide

Guidance literature:

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 18h;

DOI:10.1021/jm010531d

upstream raw materials:

D-methionine

di-tert-butyl dicarbonate

Downstream raw materials:

Boc-D-Met-OSu

(S)-2-(2-Isobutoxycarbonylamino-acetylamino)-3-phenyl-propionic acid methyl ester

Boc-D-Met-Gly-Phe-OMe

Boc-L-Met-Gly-Phe-OMe

Refernces

• 1、 Macdonald, Simon J. F.,Clarke, Geoffrey D. E.,Dowle, Michael D.,Harrison, Lee A.,Hodgson, Simon T.,Inglis, Graham G. A.,Johnson, Martin R.,Shah, Prit,Upton, Richard J.,Walls, Steven B.. "A flexible, practical, and stereoselective synthesis of enantiomerically pure trans-5-oxohexahydropyrrolo[3,2-b]pyrroles (pyrrolidine-trans-lactams), a new class of serine protease inhibitors, using acyliminium methodology". . p. 5166 - 5175. Retrieved 2007/10/03.
• 2、 Williams,Leeson,Hannah,Baker. "Resolution and synthesis of the individual enantiomers of the glycine antagonist 3-amino-1-hydroxypyrrolidin-2-one (HA-966)". . p. 1740 - 1742. Retrieved 2007/10/02.