Methyl (2S)-[[(benzyloxy)carbonyl]amino](dimethoxyphosphoryl)ethanoate

Base Information

• Chemical Name: Methyl (2S)-[[(benzyloxy)carbonyl]amino](dimethoxyphosphoryl)ethanoate
• CAS No.: 88568-95-0
• Molecular Formula: C₁₃H₁₈NO₇P
• Molecular Weight: 331.262
• Hs Code.: 29242990
• DSSTox Substance ID: DTXSID401008227
• Wikidata: Q72516371
• Mol file: 88568-95-0.mol

Synonyms:DTXSID401008227;AKOS025117460;CS-W002215;GS-6914;methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-2-(dimethyl phosphono)acetate;Methyl {[(benzyloxy)(hydroxy)methylidene]amino}(dimethoxyphosphoryl)acetate;METHYL (2S)-[[(BENZYLOXY)CARBONYL]AMINO](DIMETHOXYPHOSPHORYL)ETHANOATE

Chemical Property of Methyl (2S)-[[(benzyloxy)carbonyl]amino](dimethoxyphosphoryl)ethanoate

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 2.16E-09mmHg at 25°C
• Melting Point: 77-80 °C(lit.)
• Refractive Index: 1.504
• Boiling Point: 480.5 °C at 760 mmHg
• PKA: 9.42±0.46(Predicted)
• Flash Point: 244.4 °C
• Density: 1.284 g/cm³
• Storage Temp.: 2-8°C
• Solubility.: Soluble in methanol.
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 331.08208891
• Heavy Atom Count: 22
• Complexity: 415

Purity/Quality:

99% ^*data from raw suppliers

Z-α-Phosphonoglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 22-24/25-36-26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C(NC(=O)OCC1=CC=CC=C1)P(=O)(OC)OC
• Isomeric SMILES: COC(=O)[C@@H](NC(=O)OCC1=CC=CC=C1)P(=O)(OC)OC
• Uses: Starting material for the synthesis of (Z)-dehydroamino acids by Wittig-Horner reaction with aldehydes; the dehydroamino acids can be stereoselectively reduced to amino acids Z-α-Phosphonoglycine is used in the synthesis of calcitonin gene-related peptide antagonists. Also used in the synthesis of dehydroamino acid esters for amino acid and peptide research.

Technology Process of Methyl (2S)-[[(benzyloxy)carbonyl]amino](dimethoxyphosphoryl)ethanoate

There total 8 articles about Methyl (2S)-[[(benzyloxy)carbonyl]amino](dimethoxyphosphoryl)ethanoate 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: 90.0%

methyl 2-(benzyloxycarbonylamino)-2-methoxyacetate (127357-37-3,58237-86-8) + phosphorous acid trimethyl ester (121-45-9) → N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester (100945-15-1,88568-95-0)

Guidance literature:

methyl 2-(benzyloxycarbonylamino)-2-methoxyacetate; With phosphorus trichloride; In toluene; at 70 ℃; for 12h;

phosphorous acid trimethyl ester; In toluene; at 70 ℃; for 4h;

Reference yield:

O-benzyl carbamate (621-84-1) → N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester (100945-15-1,88568-95-0)

Guidance literature:

Multi-step reaction with 2 steps

1.2: H⁺

2.1: 85 percent / PCl₃

With phosphorus trichloride;

DOI:10.1021/jo0106593

Reference yield:

phosphorous acid trimethyl ester (121-45-9) + methyl N-benzyloxycarbonyl-α-triphenylphosphonioglycinate tetrafluoroborate → C19H18P(1+)*C12H15NO7P(1-) + N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester (100945-15-1,88568-95-0)

Guidance literature:

phosphorous acid trimethyl ester; methyl N-benzyloxycarbonyl-α-triphenylphosphonioglycinate tetrafluoroborate; With methyl-triphenylphosphonium iodide; In dichloromethane; at 20 - 45 ℃;

With methyl iodide; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1016/j.tetlet.2006.03.051

upstream raw materials:

methyl 2-(benzyloxycarbonylamino)-2-methoxyacetate

phosphorous acid trimethyl ester

N-(benzyloxycarbonyl)-α-hydroxy-glycine methyl ester

O-benzyl carbamate

Downstream raw materials:

(E)-methyl 2-(((benzyloxy)carbonyl)amino)-3-methylpent-2-enoate

(Z)-methyl 2-(((benzyloxy)carbonyl)amino)-3-methylpent-2-enoate

2-Benzyloxycarbonylamino-3-ethoxycarbonyl-but-2-enedioic acid 4-ethyl ester 1-methyl ester

(2Z,6Z)-2,7-bis(benzyloxycarbonylamino)-octa-2,6-diene-1,8-dioic acid dimethyl ester

Refernces

• 1、 Reutzel, Jan,Diogo, Timm M.,Geyer, Armin. "Reversible Folding of a β-Hairpin Peptide by a Metal-Chelating Amino Acid". supporting information. p. 8450 - 8456. Retrieved 2017/06/28.
• 2、 Berwe, Mathias,Joentgen, Winfried,Krueger, Jochen,Cancho-Grande, Yolanda,Lampe, Thomas,Michels, Martin,Paulsen, Holger,Raddatz, Siegfried,Weigand, Stefan. "Scalable synthesis of the desoxy-biphenomycin B core". experimental part. p. 1348 - 1357. Retrieved 2012/01/12.