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(S)-N-Boc-Pyroglutamic acid tert-butyl ester - CAS 91229-91-3

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Category
Main Product
Product Name
(S)-N-Boc-Pyroglutamic acid tert-butyl ester
Catalog Number
91229-91-3
Synonyms
DI-TERT-BUTYL (2S)-5-OXOPYRROLIDINE-1,2-DICARBOXYLATE;BOC-(2S)-PYROGLUT-TBU;BOC-S-PYR-OTBU;BOC-L-PYR-OTBU;(S)-N-BOC-PYROGLUTAMIC ACID TERT-BUTYL ESTER;(S)-N-ALPHA-T-BUTYLOXYCARBONYL-PYROGLUTAMIC ACID T-BUTYL ESTER;(S)-N-ALPHA-TERT-BUTYLOXYCARBONYL-PYROGL
CAS Number
91229-91-3
Molecular Weight
285.34
Molecular Formula
C14H23NO5
COA
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MSDS
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Structure
CAS 91229-91-3 (S)-N-Boc-Pyroglutamic acid tert-butyl ester
Specification
Purity
95%
Boiling Point
396.9ºC at 760 mmHg
Density
1.102
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Reference Reading
1.Rigid dipeptide surrogates: syntheses of enantiopure quinolizidinone and pyrroloazepinone amino acids from a common diaminodicarboxylate precursor.
Gosselin F1, Lubell WD. J Org Chem. 2000 Apr 7;65(7):2163-71.
A versatile and practical approach for synthesizing azabicyclo[X.Y.0]alkane amino acids of different ring sizes from a common diaminodicarboxylate precursor has been developed as a means for mimicking different peptide conformations. (2S,9S)-1-tert-Butyl 10-benzyl 5-oxo-2-[N-(PhF)amino] 9-[N-(BOC)amino]dec-4-enedioate (18) was first prepared in 83% yield by the Horner-Wadsworth-Emmons olefination of N-(PhF)aspartate beta-aldehyde 8 with pyroglutamate-derived beta-keto phosphonate 12 (PhF = 9-phenylfluoren-9-yl). The practicality of this approach for making azabicyclo[X.Y.0]alkane amino acids was then illustrated by the first synthesis of enantiopure quinolizidin-2-one amino acid 6 in seven steps and 40% overall yield from L-pyroglutamic acid. Hydrogenation of delta-keto alpha,omega-diaminosebacate 18, followed by lactam cyclization and protection, gave quinolizidin-2-one amino acid 6 as a single diastereomer. The versatility of this approach was next demonstrated by the synthesis of both ring-fusion isomers of pyrroloazepin-2-one amino acid 6 in 11 steps and 13% overall yield from pyroglutamic acid.
2.An efficient synthesis of the constrained peptidomimetic 2-oxo-3-(N-9-fluorenyloxycarbonylamino)-1-azabicyclo[4.3.0]nonane-9-carboxylic acid from pyroglutamic acid.
Mandal PK1, Kaluarachchi KK, Ogrin D, Bott SG, McMurray JS. J Org Chem. 2005 Nov 25;70(24):10128-31.
[reaction: see text] Azabicyclo[X.Y.0]alkane amino acids are rigid dipeptide mimetics that are useful tools for structure-activity studies in peptide-based drug discovery. Herein, we report an efficient synthesis of three diastereomers of 9-tert-butoxycarbonyl-2-oxo-3-(N-tert-butoxycarbonylamino)-1-azabicyclo[4.3.0]nonane (3S,6S,9S, 3S,6R,9R, and 3S,6R,9S). Methyl N-Boc-pyroglutamate is cleaved with vinylmagnesium bromide to produce an acyclic gamma-vinyl ketone. Michael addition of N-diphenylmethyleneglycine tert-butyl ester produces the N-Boc-delta-oxo-alpha,omega-diaminoazelate intermediate, which, on hydrogenloysis, gives the fused ring system. Acidolytic deprotection followed by Fmoc-protection provided building blocks suitable for solid-phase synthesis.
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