132549-37-2

Upstream product

• 132549-34-9 (S)-((4S,5R)-4-Benzyl-2-oxo-oxazolidin-5-yl)-iodo-acetic acid methyl ester 
• 28709-70-8 N-benzyloxycarbonyl-L-phenylalanine ethyl ester 
• 111871-62-6 (Z)-(S)-4-Benzyloxycarbonylamino-5-phenyl-pent-2-enoic acid methyl ester 
• 146552-53-6 2-deoxy-3,4:5,6-O-diisopropylidene-2-methoxycarbonylamino-D-glucose dimethyl acetal 
• 146552-54-7 2-deoxy-3,4-O-isopropylidene-2-methoxycarbonylamino-D-glucose dimethyl acetal 
• 146552-55-8 2-deoxy-3,4-O-isopropylidene-2-methoxycarbonylamino-D-xylose dimethyl acetal 
• 146552-56-9 (2R,3R,4S)-5-iodo-3,4-isopropylidenedioxy-2-methoxycarbonylaminopentanal dimethyl acetal 
• 146552-57-0 (2R,3S)-3-hydroxy-2-methoxycarbonylamino-4-pentenal dimethyl acetal 
• 146552-58-1 (4R,5S)-2-oxo-5-vinyl-oxazolidine-4-carbaldehyde dimethyl acetal 
• 124754-71-8 (4S,5S)-4-benzyl-5-(2-hydroxyethyl)-2-oxazolidinone 
• 186581-53-3 diazomethane 
• 72155-54-5 2-oxazolidinone of 4(S)-amino-3(S)-hydroxy-5-phenylpentanoic acid 
• 59830-60-3 benzyl (1S)-(1-formyl-2-phenylethyl)carbamate 

Downstream Products

• 72155-50-1 (3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid 

Relevant academic research and scientific papers

Synthesis of (3S,4S)-statine and a related compound, (3S,4S)-AHPPA, from D-glucosamine as a chiral pool

Biologically important threo-β-hydroxy-γ-amino acids, (3S,4S)-statine ((3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid) (1) and (3S,4S)-AHPPA (3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid) (2), were synthesized starting from D-glucosamine (3) as a chiral pool. Two routes for the transformation of D-glucosamine to key intermediates, which are applicable to the synthesis of threo-β-hydroxy-γ-amino acids, were investigated. The successful route involved C(6)-carbon degradation and elimination of the C(4)-hydroxy group of D-glucosamine in 8 steps and 30% overall yield to furnish (4R,5S)-2-oxo-5-vinyloxazolidine-4-carbaldehyde dimethyl acetal (17), which has been utilized as a versatile intermediate for synthesizing the target compounds.

Enantiospecific Synthesis of (3S,4S)-Statine and Its Analogue from D-Glucosamine as a Chiral Pool

The C(6)-carbon degradation and elimination C(4)-hydroxy group of D-glucosamine were achieved in 8-steps and 30percent overall yield to furnish (4R,5S)-5-vinyl-2-oxazolidinone-4-carbaldehyde dimethyl acetal, which was utilized as a key intermediate for en

A stereoselective synthesis of (3S,4S) statine and related compounds

(3S,4S)Statine and (3S,4S)AHPPA were synthesized efficiently using a highly stereoselective iodocyclocarbamation of the chiral Z-olefins 6 and 6b derived from the correspondent α-aminoacids.