137105-97-6

Basic information

• Product Name: (R)-3-BOC-AMINO-GAMMA-BUTYROLACTONE
• Synonyms: (R)-3-BOC-AMINO-GAMMA-BUTYROLACTONE;(R)-tert-Butyl (5-oxotetrahydrofuran-3-yl)carbaMate;tert-butyl N-[(3R)-5-oxooxolan-3-yl]carbamate
• CAS NO: 137105-97-6
• Molecular Formula: C₉H₁₅NO₄
• Molecular Weight: 201.2197
• Mol File: 137105-97-6.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (R)-3-BOC-AMINO-GAMMA-BUTYROLACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-BOC-AMINO-GAMMA-BUTYROLACTONE(137105-97-6)
• EPA Substance Registry System: (R)-3-BOC-AMINO-GAMMA-BUTYROLACTONE(137105-97-6)

Safety Data

• Hazardous Substances Data: 137105-97-6(Hazardous Substances Data)

Usage

General Description

(R)-3-BOC-AMINO-GAMMA-BUTYROLACTONE, also known as Boc-GABA, is a chemical compound with a molecular formula of C9H15NO4. It is a derivative of gamma-aminobutyric acid (GABA) and is commonly used as a building block for the synthesis of various pharmaceuticals and biologically active compounds. Boc-GABA is a white to off-white crystalline powder that is soluble in organic solvents and is stable under normal conditions. It is commonly used in the production of GABA derivatives, which have potential applications in the treatment of various neurological and psychiatric disorders. Furthermore, Boc-GABA is also used in the preparation of peptide and amino acid compounds in organic synthesis.

Upstream product

• 383418-08-4 3-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-thiobutyric acid S-ethyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 154748-49-9 3-(tert-butyloxycarbonylamino)cyclobutan-1-one 
• 1469-70-1 allyl ethyl carbonate 
• 182748-72-7 (R)-3-((tert-butoxycarbonyl)amino)-4-hydroxybutyric acid benzyl ester 

Downstream Products

• 1026304-89-1 (2R,3R)-2-benzyl-3-(tert-butyloxycarbonylamino)-4-(methanesulfonyloxy)butanoic acid tert-butyl thioester 
• 368867-83-8 (αR,4R)-α-benzyl-2-oxo-1,3-oxazolidine-4-acetic acid tert-butyl thioester 
• 368867-81-6 (3R,4R)-3-benzyl-4-(tert-butyloxycarbonylamino)-γ-butyrolactone 

Relevant articles and documents

Self-assembled ion-pair organocatalysis - Asymmetric Baeyer-Villiger oxidation mediated by flavinium-cinchona alkaloid dimer

An ion-pair catalyst generated by assembly of a chiral flavinium and a cinchona alkaloid dimer for use in asymmetric Baeyer-Villiger oxidation is presented. Ion-pair formation is essential for enhancing the catalytic activity and stereoselectivity. The catalyst is applicable to structurally diverse 3-substituted cyclobutanones, providing good to excellent enantioselectivities (up to 98: 2 e.r.). This study provides the first example of self-assembly of a flavin derivative and a base to form a chiral reaction site that enables a highly stereoselective reaction to occur.

The synthesis of Fmoc-O-allyl β-serine

Two concise routes for the synthesis of the title amino acid have been developed. The first route employs Seebach's general approach [Seebach, D.; Lelais, G.; Micuch, P.; Josien-Lefebvre, D.; Rossi, F. Helv. Chim. Acta 2004, 87, 3131] with Arndt Eistert h