161365-10-2

Upstream product

• 3587-60-8 Benzyloxymethyl chloride 
• 33985-40-9 1-O-methyl-2,3-O-isopropylidene-α-D-mannopentoaldo-1,4-furanose 
• 27954-10-5 methyl 2,3-O-isopropylidene-α-D-mannofuranoside 
• 220051-10-5 methyl 5,6-anhydro-2,3-O-isopropylidene-α-D-mannofuranoside 
• 100-51-6 benzyl alcohol 
• 40789-24-0 methyl 2,3-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-mannofuranoside 
• 100-39-0 benzyl bromide 

Downstream Products

• 497234-45-4 methyl (5R)-6-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-2,3-O-isopropylidene-α-D-mannofuranoside 
• 497234-46-5 methyl (5S)-6-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-2,3-O-isopropylidene-β-L-gulofuranoside 
• 497234-43-2 methyl (5R)-6-O-benzyl-5-(dimethoxyphosphinyl)-2,3-O-isopropylidene-α-D-lyxo-hexofuranoside 
• 497234-44-3 methyl (5S)-6-O-benzyl-5-(dimethoxyphosphinyl)-2,3-O-isopropylidene-α-D-lyxo-hexofuranoside 
• 497234-42-1 methyl 6-O-benzyl-2,3-O-isopropylidene-α-D-lyxo-hexofuranosid-5-ulose 

Relevant academic research and scientific papers

Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (α-hydroxyphosphonates)

The addition of dimethyl phosphonate to six different hexofuranos-5-uloses in the presence of DBU, followed by esterification with methoxalyl chloride and then radical reduction, afforded 5-deoxy-5-dimethoxyphosphinyl-D- and L-hexofuranoses. The stereosel

A new route for preparation of 5-deoxy-5-(hydroxyphosphinyl)-D-mannopyranose and -L-gulopyranose derivatives

Starting from methyl 2,3-O-isopropylidene-α-D-mannofuranoside (5), methyl 6-O-benzyl-2,3-O-isopropylidene-α-D-lyxo-hexofuranosid-5-ulose (12) was prepared in three steps. The addition reaction of dimethyl phosphonate to 12, followed by deoxygenation of 5-

Elongation of the pentose chain at the terminal carbon atom with Grignard C1 reagents. A study of the homologation reaction

Derivatives of four stereoisomeric pentodialdo-1,4-furanoses were reacted with four Grignard C1 reagents: methoxymethyl-, allyloxymethyl-, benzyloxymethyl, and dimethylphenylsilylmethyl-magnesium chlorides. Derivatives of the expected stereoisomeric hexoses were accompanied in some cases by C-4 inverted products. The results have been discussed in terms of α- and β-chelated transition states. It has been found that the RX (X=O,Si) grouping of the Grignard reagent strongly influences the stereochemical outcome of the elongation reaction.

A convenient preparation of 5-benzyl ethers of D-gluco- and D-manno-furanose derivatives

Keywords: Glucofuranose; Mannofuranose; Selective benzylation; Two-phase benzylation