Carboxymethylglycoside lactones (CMGLs): structural variations on the carbohydrate moiety

New glucose and galactose based bicyclic lactones, with variations in the anomeric configuration, the protecting groups (acetyl or benzyl) and the furanosyl or pyranosyl rings were synthesized from allyl glycosides and used for the preparation of a series of new glycosylated alkyne amides.

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Carboxymethyl-3,4,6-tri-O-acetyl-α-d-galactopyranoside-2-O-lactoneC14H18O10Ee = 100%[α]D=+113[α]D=+113 (c 0.9, CHCl3)Source of chirality: allyl-α-d-galactopyranoside

Carboxymethyl-3,4,6-tri-O-acetyl-β-d-glucopyranoside-2-O-lactoneC14H18O10Ee = 100%[α]D=+93[α]D=+93 (c 1, CH2Cl2)Source of chirality: allyl-β-d-glucopyranoside

Carboxymethyl-3,4,6-tri-O-acetyl-β-d-galactopyranoside-2-O-lactoneC14H18O10Ee = 100%[α]D=+85[α]D=+85 (c 1, CHCl3)Source of chirality: allyl-β-d-galactopyranoside

Carboxymethyl-3,4,6-tri-O-benzyl-β-d-glucopyranoside-2-O-lactoneC29H30O7Ee = 100%[α]D=-21[α]D=-21 (c 1, CHCl3)Source of chirality: allyl-β-d-glucopyranoside

Carboxymethyl-3,4,6-tri-O-benzyl-β-d-galactopyranoside-2-O-lactoneC29H30O7Ee = 100%[α]D=+51[α]D=+51 (c 0.2, CHCl3)Source of chirality: allyl-β-d-galactopyranoside

Carboxymethyl-3,4,6-tri-O-benzyl-α-d-glucopyranoside-2-O-lactoneC29H30O7Ee = 100%[α]D=+88[α]D=+88 (c 0.8, CHCl3)Source of chirality: allyl-α-d-glucopyranoside

Carboxymethyl-3,4,6- tri-O-benzyl-α-d-galactopyranoside-2-O-lactoneC29H30O7Ee = 100%[α]D=+71[α]D=+71 (c 0.8, CHCl3)Source of chirality: allyl-α-d-galactopyranoside

Carboxymethyl-3,5,6-tri-O-benzyl-α-d-glucofuranoside-2-O-lactoneC29H30O7Ee = 100%[α]D=+19[α]D=+19 (c 0.7, CHCl3)Source of chirality: allyl-α-d-glucofuranoside

(N-Propargylcarbamoyl)methyl-3,4,6-tri-O-acetyl-α-d-galactopyranosideC17H23O10NEe = 100%[α]D=+122[α]D=+122 (c 0.6, CHCl3)Source of chirality: carboxymethyl-3,4,6-tri-O-acetyl-α-d-galactopyranoside-2-O-lactone

(N-Propargylcarbamoyl)methyl-3,4,6-tri-O-acetyl-β-d-galactopyranosideC17H23O10NEe = 100%[α]D=-2[α]D=-2 (c 0.6, CHCl3)Source of chirality: carboxymethyl-3,4,6-tri-O-acetyl-β-d-galactopyranoside-2-O-lactone

(N-Propargylcarbamoyl)methyl-3,4,6-tri-O-benzyl-β-d-glucopyranosideC32H35O7NEe = 100%[α]D=+5[α]D=+5 (c 0.3, CHCl3)Source of chirality: carboxymethyl-3,4,6-tri-O-benzyl-β-d-glucopyranoside-2-O-lactone

(N-Propargylcarbamoyl)methyl-3,4,6-tri-O-benzyl-β-d-galactopyranosideC32H35O7NEe = 100%[α]D=+3[α]D=+3 (c 1, CHCl3)Source of chirality: carboxymethyl-3,4,6-tri-O-benzyl-β-d-galactopyranoside-2-O-lactone

(N- Propargylcarbamoyl)methyl-3,4,6-tri-O-benzyl-α-d-glucopyranosideC32H35O7NEe = 100%[α]D=+88[α]D=+88 (c 0.5, CHCl3)Source of chirality: carboxymethyl-3,4,6-tri-O-benzyl-α-d-glucopyranoside-2-O-lactone

(N-Propargylcarbamoyl)methyl-3,4,6-tri-O-benzyl-α-d-galactopyranosideC32H35O7NEe = 100%[α]D=+84[α]D=+84 (c 0.6, CHCl3)Source of chirality: carboxymethyl-3,4,6-tri-O-benzyl-α-d-galactopyranoside-2-O-lactone

(N-Propargylcarbamoyl)methyl-3,4,6-tri-O-benzyl-α-d-glucofuranosideC32H35O7NEe = 100%[α]D=+10[α]D=+10 (c 0.9, CHCl3)Source of chirality: carboxymethyl-3,5,6-tri-O-benzyl-α-d-glucofuranoside-2-O-lactone

(N-Propargylcarbamoyl)methyl-α-d-glucopyranosideC11H17O7NEe = 100%[α]D=+188[α]D=+188 (c 1, H2O)Source of chirality: (N-propargylcarbamoyl)methyl-3,4,6-tri-O-acetyl-α-d-glucopyranoside

N-Methyl[-4-[1-(5′-deoxyuridin)-1,2,3-triazole]]carbamoylmethyl α-d-glucopyranosideC20H28O12N6Ee = 100%[α]D=+89[α]D=+89 (c 1, H2O)Source of chirality: (N-propargylcarbamoyl)methyl-α-d-glucopyranoside