100945-15-1

Basic information

• Product Name: N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester
• Synonyms: N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester
• CAS NO: 100945-15-1
• Molecular Weight: 331.262
• Mol File: 100945-15-1.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester(100945-15-1)
• EPA Substance Registry System: N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester(100945-15-1)

Safety Data

• Hazardous Substances Data: 100945-15-1(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 142696-31-9 (E)-2-Benzyloxycarbonylamino-3-(2,2-dimethyl-[1,3]dioxolan-4-yl)-acrylic acid methyl ester 
• 142696-32-0 (Z)-2-Benzyloxycarbonylamino-3-(2,2-dimethyl-[1,3]dioxolan-4-yl)-acrylic acid methyl ester 
• 135345-94-7 (S)-Benzyloxycarbonylamino-((3aS,4S,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetic acid methyl ester 
• 135345-95-8 (R)-Benzyloxycarbonylamino-((3aS,4S,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetic acid methyl ester 
• 142056-00-6 (E)-2-Benzyloxycarbonylamino-but-2-enedioic acid 4-tert-butyl ester 1-methyl ester 
• 142056-02-8 (Z)-2-Benzyloxycarbonylamino-but-2-enedioic acid 4-tert-butyl ester 1-methyl ester 
• 135346-03-1 (S)-Benzyloxycarbonylamino-((3aS,4S,6R,6aR)-2,2-dimethyl-6-trityloxymethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetic acid methyl ester 
• 135346-00-8 (R)-Benzyloxycarbonylamino-((3aS,4S,6R,6aR)-2,2-dimethyl-6-trityloxymethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetic acid methyl ester 
• 89525-23-5 methyl (Z)-2-((benzyloxycarbonyl)amino)-2-pentenoate 
• 142602-48-0 methyl 2-(((benzyloxy)carbonyl)amino)pent-2-enoate 
• 176504-51-1 methyl (2Z)-2-{[(benzyloxy)carbonyl]amino}-3-(3,5-difluorophenyl) acrylate 
• 116835-82-6 methyl (Z)-2-carbobenzoxyamino-3-(4-methoxyphenyl)acrylate 
• 132970-32-2 methyl (4S,2Z)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentanoate 
• 220854-85-3 (Z)-2-Benzyloxycarbonylamino-3-[6-((Z)-2-benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-pyridin-2-yl]-acrylic acid methyl ester 

Relevant articles and documents

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.

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.

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%.