88568-95-0

Basic information

• Product Name: (+/-)-BENZYLOXYCARBONYL-ALPHA-PHOSPHONOGLYCINE TRIMETHYL ESTER
• Synonyms: 2-(DiMethoxyphosphinyl)-2-[[(benzyloxy)carbonyl]aMino]acetic acid Methyl ester;Benzyloxycarbonyl-alpha-phosphonoglycinetriMethyl es;(+/-)-BENZYLOXYCARBONYL-ALPHA-PHOSPHONOGLYCINE;Methyl 2-(((benzyloxy)carbonyl)aMino)-2-(diMethoxyphosphoryl)acetate;Z-Gly(PO(OME2))-OMe;(±Acetic acid, 2-(dimethoxyphosphinyl)-2-[[(phenylmethoxy)carbonyl]amino]-, methyl ester;Cbz-a-phosphono-glycine trimethyl ester
• CAS NO: 88568-95-0
• Molecular Formula: C13H18NO7P
• Molecular Weight: 331.26
• EINECS: 1308068-626-2
• Mol File: 88568-95-0.mol

Chemical Properties

• Melting Point: 77-80 °C(lit.)
• Boiling Point: 480.5 °C at 760 mmHg
• Flash Point: 244.4 °C
• Appearance: White/Crystalline Powder
• Density: 1.284 g/cm³
• Vapor Pressure: 2.16E-09mmHg at 25°C
• Refractive Index: 1.504
• Storage Temp.: 2-8°C
• Solubility: Soluble in methanol.
• PKA: 9.42±0.46(Predicted)
• BRN: 5764460
• CAS DataBase Reference: (+/-)-BENZYLOXYCARBONYL-ALPHA-PHOSPHONOGLYCINE TRIMETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-BENZYLOXYCARBONYL-ALPHA-PHOSPHONOGLYCINE TRIMETHYL ESTER(88568-95-0)
• EPA Substance Registry System: (+/-)-BENZYLOXYCARBONYL-ALPHA-PHOSPHONOGLYCINE TRIMETHYL ESTER(88568-95-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 22-24/25-36-26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 88568-95-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(+/-)-Benzyloxycarbonyl-alpha-phosphono-glycine trimethyl ester is used as a key intermediate in the synthesis of calcitonin gene-related peptide antagonists. These antagonists have potential therapeutic applications in treating various conditions, such as pain and inflammation.
Used in Amino Acid and Peptide Research:
(+/-)-BENZYLOXYCARBONYL-ALPHA-PHOSPHONOGLYCINE TRIMETHYL ESTER is also utilized in the synthesis of dehydroamino acid esters, which are essential for amino acid and peptide research. The ability to produce dehydroamino acids selectively allows for the development of new methods and techniques in the field of organic chemistry and biochemistry.
Used in Organic Synthesis:
(+/-)-Benzyloxycarbonyl-alpha-phosphono-glycine trimethyl ester serves as a valuable starting material for the synthesis of (Z)-dehydroamino acids through the Wittig-Horner reaction with aldehydes. This reaction is a widely used method for the preparation of various organic compounds, including those with potential applications in medicine, agriculture, and other industries.

InChI:InChI=1/C13H18NO7P/c1-18-12(15)11(22(17,19-2)20-3)14-13(16)21-9-10-7-5-4-6-8-10/h4-8,11H,9H2,1-3H3,(H,14,16)/t11-/m1/s1

Upstream product

• 127357-37-3 methyl 2-(benzyloxycarbonylamino)-2-methoxyacetate 
• 64356-76-9 N-benzyloxycarbonyl α-chloro glycine methyl ester 
• 121-45-9 phosphorous acid trimethyl ester 
• 621-84-1 O-benzyl carbamate 
• 79002-45-2 N-benzyloxycarbonyl-glycine 
• 127357-38-4 N-(benzyloxycarbonyl)-α-hydroxy-glycine methyl ester 

Downstream Products

• 121056-95-9 trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate 
• 590369-87-2 methyl 6-chloroisoquinoline-3-carboxylate 
• 950224-79-0 methyl β-[(2-aminophenyl)thio]-N-[(benzyloxy)carbonyl]-2,5-difluorophenylalaninate 

Relevant articles and documents

Preparation method of Wittig-Horner reagent

A preparation method of a Wittig-Horner reagent is disclosed. According to the preparation method of the Wittig-Horner reagent provided by the invention, a compound with a structure as shown in a formula (I) and a glyoxylic acid aqueous solution with a sp

Reversible Folding of a β-Hairpin Peptide by a Metal-Chelating Amino Acid

5-(1-Hydroxy-pyridin-2(1H)-onyl)-l-alanine (Hop) is a N-hydroxy-1,2-pyridone functionalized α-amino acid with the desired metal-chelating properties of DOPA (3,4-dihydroxy phenylalanine) but without its unwanted redox activity. The Fmoc-protected amino acid Fmoc-l-Hop(tBu)-OH (11) was synthesized from glycine phosphonate followed by enzymatic hydrolysis of the methyl ester yielding the Hop l-isomer in 96 % ee. The amino acid 11 is used in automated peptide synthesis for the assembly of a 14mer β-hairpin peptide with the sequence [dsb1, 14]H-CHXETGKHGHKLVC-OH (X=W, l-Hop). While the 10 π electron containing indole side chain of l-Trp in peptide 14 completes the formation of a hydrophobic cluster and results in 90 % folding, the folded fraction is significantly decreased to approximately 30 % for the 6 π electron l-Hop side chain in peptide 16. Metal chelation of Ga3+ reconstitutes the folding of 16 to above 60 % due to the formation of the Ga(16)3 trimer. The chelation process of 16 is monitored by NMR spectroscopy and the subsequent release of Ga3+ by a competitive metal chelator exemplifies the reversible oligomerization of peptide epitopes by metal chelation, bearing the opportunity to synthesize protein-sized aggregates on the basis of reversible chemistry in water.

SUBSTITUTED HETEROCYCLIC ACETAMIDES AS KAPPA OPIOID RECEPTOR (KOR) AGONISTS

The present invention relates to a series of substituted compounds having the general formula (I), including their ste reoisomers and/or their pharmaceutically acceptable salts, wherein R1, R2, R3. R4, R5, and R6 are as defined herein. This invention also relates to methods of making these compounds including intermediates. The compounds of this invention are effective at the kappa (κ) opioid receptor (KOR) site. Therefore, the compounds of this invention are useful as pharmaceutical agents, especially in the treatment and/or prevention of a variety of central nervous system disorders (CNS), including but not limited to acute and chronic pain, and associated disorders, particularly functioning peripherally at the CNS.

Scalable synthesis of the desoxy-biphenomycin B core

We describe the evolution of a kilogram-scale synthesis of the protected cyclic tripeptide desoxy-biphenomycin B, based on an early discovery route. The retrosynthetic concept included a macrolactamization strategy to build the core ring system of biphenomycin B in combination with a double catalytic asymmetric hydrogenation protocol for the construction of the ansa-tripeptide precursor. Eventually, the kilogram process comprised a 16-step sequence with an overall yield for the longest linear sequence of 19.5%.

Stereocontrolled total synthesis of (-)-kaitocephalin

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A new convenient synthesis of N-acyl-2-(dimethoxyphosphoryl)glycinates

Easily accessible N-acyl-2-triphenylphosphonioglycinate tetrafluoroborates react smoothly with trimethylphosphite in the presence of methyltriphenylphosphonium iodide to give N-acyl-2-(dimethoxyphosphoryl)glycinates in good or very good yields. The dimeth

COMPOUNDS HAVING BOTH α7 NICOTINIC AGONIST ACTIVITY AND 5HT3 ANTAGONIST ACTIVITY FOR TREATMENT OF CNS DISEASES

The invention discloses compounds that are selective α7 nAChR agonists and 5-HT3 antagonists. The compounds are useful for treating many CNS diseases.

Substituted 7-aza[2.2.1]bicycloheptanes for the treatment of disease

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Total synthesis of isoroquefortine C

A short and efficient total synthesis of isoroquefortine C, the 3,12-(Z)-isomer of roquefortine C, from L-tryptophan methyl ester hydrochloride and 4(5)-(hydroxy)methylimidazole hydrochloride is described.