104473-51-0

Basic information

• Product Name: ethyl 2-(((benzyloxy)carbonyl)amino)-2-hydroxyacetate
• Synonyms: ethyl 2-(((benzyloxy)carbonyl)amino)-2-hydroxyacetate
• CAS NO: 104473-51-0
• Molecular Weight: 253.255
• Mol File: 104473-51-0.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: ethyl 2-(((benzyloxy)carbonyl)amino)-2-hydroxyacetate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-(((benzyloxy)carbonyl)amino)-2-hydroxyacetate(104473-51-0)
• EPA Substance Registry System: ethyl 2-(((benzyloxy)carbonyl)amino)-2-hydroxyacetate(104473-51-0)

Safety Data

• Hazardous Substances Data: 104473-51-0(Hazardous Substances Data)

Upstream product

• 924-44-7 glyoxylic acid ethyl ester 
• 621-84-1 O-benzyl carbamate 
• 151-10-0 1,3-Dimethoxybenzene 
• 64805-08-9 ethyl glyoxylate hydrate 
• 28130-04-3 Z-Thr-OEt 

Downstream Products

• 62183-04-4 acetoxy-benzyloxycarbonylamino-acetic acid ethyl ester 
• 1562347-74-3 C₂₁H₂₅NO₆ 
• 1562347-77-6 ethyl N-benzyloxycarbonyl-α-(4-(dimethylamino)benzo[1,3]dioxol-5-yl)glycinate 
• 1562347-79-8 ethyl N-benzyloxycarbonyl-α-(N-metylpyrrol-2-yl)glycinate 
• 1562347-85-6 ethyl N-benzyloxycarbonyl-α-(furan-2-yl)glycinate 
• 1562351-82-9 ethyl N-benzyloxycarbonyl-α-(1-methylindol-3-yl)glycinate 
• 1562347-89-0 ethyl N-benzyloxycarbonyl-α-(1H-indol-3-yl)glycinate 
• 1562347-92-5 ethyl N-benzyloxycarbonyl-2-(anthracen-9-yl)glycinate 
• 1562347-97-0 C₁₂H₁₄⁽²⁾HNO₅ 
• 134746-23-9 ethyl 2-(((benzyloxy)carbonyl)amino)-2-chloroacetate 
• 1562347-70-9 ethyl N-benzyloxycarbonyl-α-(4-methoxyphenyl)glycinate 
• 1562347-72-1 ethyl N-benzyloxycarbonyl-α-(5-bromo-2,4-dimethoxyphenyl)glycinate 
• 1562347-65-2 ethyl N-benzyloxycarbonyl-α-(2,4-dimethoxyphenyl)glycinate 
• 60025-92-5 ethyl 2,2-bis(2,4-dimethoxyphenyl)acetate 

Relevant articles and documents

Asymmetric Mannich synthesis of α-amino esters by anion-binding catalysis

We report a scalable, one-pot Mannich route to enantioenriched α-amino esters by direct reaction of α-chloroglycine ester as a practical imino ester surrogate. The reaction is promoted by a chiral aminothiourea, which is proposed to operate cooperatively

Enantioselective Synthesis of α-Allyl Amino Esters via Hydrogen-Bond-Donor Catalysis

We report a chiral-squaramide-catalyzed enantio- and diastereoselective synthesis of α-allyl amino esters. The optimized protocol provides access to N-carbamoyl-protected amino esters via nucleophilic allylation of readily accessible α-chloro glycinates. A variety of useful α-allyl amino esters were prepared, including crotylated products bearing vicinal stereocenters that are inaccessible through enolate alkylation, with high enantioselectivity (up to 97% ee) and diastereoselectivity (>10:1). The reactions display first-order kinetic dependence on both the α-chloro glycinate and the nucleophile, consistent with rate-limiting C-C bond formation. Computational analysis of the uncatalyzed reaction predicts an energetically inaccessible iminium intermediate, and a lower energy concerted SN2 mechanism.

Catalytic Asymmetric Mannich Reaction with N-Carbamoyl Imine Surrogates of Formaldehyde and Glyoxylate

N,O-acetals (NOAcs) were developed as bench stable surrogates for N-carbamoyl, (Boc, Cbz and Fmoc) formaldehyde and glyoxylate imines in asymmetric Mannich reactions. The NOAcs can be directly utilized in the chiral primary amine catalyzed Mannich reactions of both acyclic and cyclic β-ketocarbonyls with high yields and excellent stereoselectivity. The current reaction offers a straightforward approach in the asymmetric synthesis of α- or β-amino carbonyls bearing chiral quaternary centers in a practical and highly stereocontrolled manner.