110579-36-7

Basic information

• Product Name: tert-butyl (3S,5R)-5-(broMoMethyl)-tetrahydro-2-oxofuran-3-ylcarbaMate
• Synonyms: tert-butyl (3S,5R)-5-(broMoMethyl)-tetrahydro-2-oxofuran-3-ylcarbaMate
• CAS NO: 110579-36-7
• Molecular Formula: C10H16BrNO4
• Molecular Weight: 294.14234
• Mol File: 110579-36-7.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: tert-butyl (3S,5R)-5-(broMoMethyl)-tetrahydro-2-oxofuran-3-ylcarbaMate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (3S,5R)-5-(broMoMethyl)-tetrahydro-2-oxofuran-3-ylcarbaMate(110579-36-7)
• EPA Substance Registry System: tert-butyl (3S,5R)-5-(broMoMethyl)-tetrahydro-2-oxofuran-3-ylcarbaMate(110579-36-7)

Safety Data

• Hazardous Substances Data: 110579-36-7(Hazardous Substances Data)

Upstream product

• 90600-20-7 (2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid 
• 104241-32-9 (2S,4R)-2-tert-butoxycarbonylamino-4-hydroxymethyl-4-butanolide 
• 16338-48-0 L-allylglycine 
• 104241-30-7 (2S,4S)-2-(tert-butoxycarbonyl)amino-4-bromomethyl-γ-butyrolactone 
• 104241-31-8 (2S,4S)-2-(tert-butoxycarbonyl)amino-3,4-epoxypentanoic acid methyl ester 

Relevant articles and documents

Towards a total synthesis of ustiloxins A and B. Stereocontrolled synthesis of (2S,4S,6S)-4-hydroxy-5-phenylsulfinylnorvaline

A short, stereocontrolled synthesis of (2S,4S,6S)-4-hydroxy-5-phenylsulfinylnorvaline (8), an unusual amino acid component of ustiloxins A and B, has been achieved. Stereoselective bromolactonisation of N-Boc-(S)-allylglycine (3) is followed by substitution of the bromide 4a with thiophenol to give the corresponding sulfide 5. Highly stereoselective oxidation of the sulfide 5 gives the corresponding sulfoxide 6a. Removal of the Boc group and lactone ring opening then complete the synthesis of the unusual amino acid.

AN EFFICIENT ROUTE TO 1,3-AMINO HYDROXYL SYSTEM VIA ELECTROPHILIC LACTONIZATION OF 2-AMINO-4-PENTENOIC ACID DERIVATIVES. STEREOSELECTIVE SYNTHESIS OF (-)-BULGECININE

Several γ-hydroxy-α-amino acid systems were prepared stereoselectively from 2-amino-4-pentenoic acid derivatives using electrophilic lactonization.This strategy was applied to the synthesis of a highly functionalized proline analogue, (-)-bulgecinine (4).