620173-69-5

Upstream product

• 108-24-7 acetic anhydride 
• 64552-06-3 methyl 4,6-O-benzylidene-α-D-galactopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 3396-99-4 methyl α-D-galactopyranoside 

Downstream Products

• 1195290-71-1 methyl-(O²,O³-diacetyl-O⁶-trityl-α-D-galactopyranoside) 
• 60534-70-5 sorbistin A₁ 
• 77594-09-3 Acetic acid (2S,3R,4S,5R,6S)-3-acetoxy-5-azido-2-methoxy-6-trityloxymethyl-tetrahydro-pyran-4-yl ester 
• 77594-08-2 methyl 2,3-di-O-acetyl-4-O-mesyl-6-O-trityl-α-D-galactopyranoside 
• 77594-15-1 Propionic acid (2S,3R,4S,5R,6R)-3-amino-6-[(1S,2R,3S)-2-amino-1-((S)-2-amino-1-hydroxy-ethyl)-3,4-dihydroxy-butoxy]-4,5-bis-benzyloxy-tetrahydro-pyran-2-ylmethyl ester 
• 77594-17-3 Propionic acid (2S,3R,4S,5R,6R)-3-amino-6-((1S,2S,3R,4S)-3-amino-1-aminomethyl-2,4,5-trihydroxy-pentyloxy)-4,5-bis-benzyloxy-tetrahydro-pyran-2-ylmethyl ester 
• 77594-16-2 N-{(2S,3R,4S,5R,6R)-6-[(1S,2R,3S)-2-Amino-1-((S)-2-amino-1-hydroxy-ethyl)-3,4-dihydroxy-butoxy]-4,5-bis-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yl}-propionamide 
• 77594-18-4 N-[(2S,3R,4S,5R,6R)-6-((1S,2S,3R,4S)-3-Amino-1-aminomethyl-2,4,5-trihydroxy-pentyloxy)-4,5-bis-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yl]-propionamide 
• 1214746-73-2 methyl 2,3-di-O-acetyl-4-O-benzoyl-α-D-galactopyranoside 
• 1214746-71-0 methyl 2,3-di-O-acetyl-6-O-benzoyl-α-D-galactopyranoside 

Relevant academic research and scientific papers

N -Glycosylation with sulfoxide donors for the synthesis of peptidonucleosides

The synthesis of glycopyranosyl nucleosides modified in the sugar moiety has been less frequently explored, notably because of the lack of a reliable method to glycosylate pyrimidine bases. Herein we report a solution in the context of the synthesis of peptidonucleosides. They were obtained after glycosylation of different pyrimidine nucleobases with glucopyranosyl donors carrying an azide group at the C4 position. A methodological study involving different anomeric leaving groups (acetate, phenylsulfoxide and ortho-hexynylbenzoate) showed that a sulfoxide donor in combination with trimethylsilyl triflate as the promoter led to the best yields.

TOTAL SYNTHESIS OF SORBISTIN A1 AND A POSITIONAL ISOMER

Total synthesis of sorbistin A1 (1) and a positional isomer (7) is described for the first time in a regio- and stereo-controlled manner.