170998-34-2

Upstream product

• 100-39-0 benzyl bromide 
• 85207-16-5 allyl 2,3-O-isopropylidene-α-D-mannopyranoside 
• 530-26-7 D-Mannose 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 119111-31-8 allyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 85207-15-4 allyl 2,3:4,6-di-O-isopropylidene-α-D-mannopyranoside 
• 41308-76-3 allyl α-D-mannopyranoside 

Downstream Products

• 493012-77-4 C₅₇H₅₁O₂₀P 
• 363619-60-7 C₅₉H₅₅O₂₀P 
• 363619-62-9 C₄₈H₅₁O₁₈P 
• 363619-65-2 C₃₇H₃₅O₁₂P 
• 363619-58-3 C₃₀H₃₁O₁₁P 
• 363619-54-9 ((3aS,4S,6R,7R,7aS)-7-Benzyloxy-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethyl)-phosphonic acid dimethyl ester 
• 363619-59-4 Benzoic acid (3aS,4S,6R,7R,7aS)-4-(dimethoxy-phosphorylmethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl ester 

Relevant academic research and scientific papers

Synthesis of β-D-Galp-(1 →4)-α-D-Manp methanephosphonate, a substrate analogue for the elongating α-D-mannosyl phosphate transferase in the Leishmania

An isosteric C-glycoside phosphono analogue of dec-9-enyl β-D-galactopyranosyl-(1 →4)-α-D-mannopyranosyl phosphate was synthesised and showed high biological activity in the Leishmania MPT assay. A one-step Horner-Emmons/Michael reaction was developed for the stereoselective preparation of α-D-mannosyl methanephosphonate derivatives.

EFFECT OF PROTECTING GROUPS AND SOLVENTS IN ANOMERIC O-ALKYLATION OF MANNOPYRANOSE

Anomeric O-alkylation of mannopyranoses with various protecting groups was investigated using mannose derivatives and 2,3-O-isopropylidene-1-O-trifluoromethanesulfonyl-D-glycerol (1) as alkylating agent.Generally, in polar solvents higher α/β ratios were obtained than in nonpolar solvents.Sterically demanding protecting groups at the 6-O-position and polar solvents led to higher yields.Reactivity differences were explained by different complex formation.Based on these results mannopyranosyl-α(1-4)glucopyranosides 26 and 27 were synthesized using mannose derivatives 5 and 6 having a 6-O-(p-methoxyphenyl)diphenylmethyl group and galactosyl trifluoromethanesulfonate 24 or nonafluorobutanesulfonate (nonaflate) 25, respectively, as alkylating agents.