549504-45-2

Basic information

• Product Name: (2S)-3-Azido-2-hydroxy-2-methyl-propanoic Acid Methyl Ester
• Synonyms: (2S)-3-Azido-2-hydroxy-2-methyl-propanoic Acid Methyl Ester
• CAS NO: 549504-45-2
• Molecular Formula: C5H9N3O3
• Molecular Weight: 0
• Product Categories: All Aliphatics;Aliphatics;Chiral Reagents
• Mol File: 549504-45-2.mol

Chemical Properties

• Appearance: /
• Solubility: Acetone, Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: (2S)-3-Azido-2-hydroxy-2-methyl-propanoic Acid Methyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-3-Azido-2-hydroxy-2-methyl-propanoic Acid Methyl Ester(549504-45-2)
• EPA Substance Registry System: (2S)-3-Azido-2-hydroxy-2-methyl-propanoic Acid Methyl Ester(549504-45-2)

Safety Data

• Hazardous Substances Data: 549504-45-2(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Liquid

Upstream product

• 356048-01-6 methyl (4R)-4-methyl-2-oxo-2λ⁴-[1,3,2]dioxathiolane-4-carboxylate 
• 356048-06-1 methyl (4R)-4-methyl-2-dioxo-2λ⁶-[1,3,2]dioxathiolane-4-carboxylate 
• 356048-02-7 (4S)-4-methyl-2-oxo-2λ⁴-[1,3,2]dioxathiolane-4-carboxylic acid methyl ester 
• 58653-97-7 methyl 2-methyl-2-oxiranecarboxylate 
• 147501-85-7 (S)-2,3-dihydroxy-2-methyl-propionic acid methyl ester 
• 147501-89-1 (R)-2,3-dihydroxy-2-methyl-propionic acid methyl ester 
• 356048-07-2 methyl (4S)-4-methyl-2-dioxo-2λ⁶-[1,3,2]dioxathiolane-4-carboxylate 

Relevant articles and documents

Enzyme-catalyzed nucleophilic ring opening of epoxides for the preparation of enantiopure tertiary alcohols

The halohydrin dehalogenase from Agrobacterium radiobacter AD1 (HheC) catalyzes nucleophilic ring opening of epoxides with cyanide and azide. In the case of 2,2-disubstituted epoxides, this reaction proceeds with excellent enantioselectivity (E values up

Enantioselective synthesis of α-methyl-D-cysteine and lanthionine building blocks via α-methyl-d-serine-β-lactone

(Matrix presented) We report here the enantioselective synthesis of Boc-α-methyl-D-cysteine(PMB)-OH and lanthionine building blocks through the regioselective ring opening of key intermediate Boc-α -methyl-D-serine-β-lactone.

Understanding the unusual regioselectivity in the nucleophilic ring-opening reactions of gem-disubstituted cyclic sulfates. Experimental and theoretical studies

The regioselectivity of the nucleophilic ring-opening reactions of three gem-disubstituted cyclic sulfates with sodium azide has been studied from both experimental and theoretical viewpoints. It is found that, depending on the substituent present in the cyclic sulfate, the reaction displays reversed regioselectivity, which allows one or another regioisomer to be obtained with selectivities greater than 4:1. The theoretical calculations show that, contrary to previous understanding, the intrinsic preference in all cases is azide attack at the less-substituted Cβ position, a consequence of similar stereoelectronic effects in the three sulfates considered. The observed preference for Cα attack in the case of the ester sulfate is explained in terms of differential solvent effects, which are in turn due to subtle differences in the charge transfer in the different transition structures.

Enantioselective synthesis of (S)- and (R)-α-methylserines: Application to the synthesis of (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals

This report describes the synthesis of enantiomerically pure (S)- and (R)-α-methylserines on a multigram scale, starting from the Weinreb amide of 2-methyl-2-propenoic acid and using a stereodivergent synthetic route that involves a Sharpless asymmetric dihydroxylation reaction. As a synthetic application of these quaternary α-amino acids, they were used as starting materials in the synthesis of the well-known valuable homochiral (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinal building blocks.