67737-49-9

Upstream product

• 917-64-6 methyl magnesium iodide 
• 67737-48-8 methyl 5-benzyloxy-β-D-ribofuranoside 
• 33019-63-5 (2R,3R,4R,5R)-2-benzyloxymethyl-3,4-isopropylidenedioxy-5-methoxytetrahydrofuran 
• 1824-96-0 methyl ribofuranoside 
• 58763-00-1 ((3aR,4R,6S,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 532-20-7 D-Ribose 
• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 81275-41-4 methyl 5-O-benzyl-2,3-O-isopropylidene-α-D-ribofuranoside 

Downstream Products

• 79083-29-7 (2R,3R,4R,5S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran 
• 86861-76-9 C₂₇H₃₀O₉S₂ 

Relevant academic research and scientific papers

Synthesis of methyl 2-O-allyl-(and 3-O-allyl-)5-O-benzyl-β-D-ribofuranoside

D-Ribose was converted into methyl 5-O-benzyl-β-D-ribofuranoside and this, on tin-mediated allylation, gave a mixture of the 2-O-allyl and 3-O-allyl derivatives which were separated by chromatography. The more polar isomer was characterised as the 3-O-allyl derivative after conversion via 3-O-allyl-5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose (which was also synthesised from 3-O-allyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose) into the known 5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose. Methyl 3-O-allyl-5-O-benzyl-β-D-ribofuranoside was converted into methyl 2-O-allyl-5-O-benzyl-β-D-ribofuranoside via methyl 2-O-allyl-5-O-benzyl-3-O(prop-1-enyl)-β-D-ribofuranoside.

The Use of Grignard Reagents in the Synthesis of Carbohydrates. III. The One-way Anomerization of Methyl Glycofuranosides and the Opening of Their Furanose Rings

The anomerization of methyl glycofuranoside derivatives with methylmagnesium iodide or t-butylmagnesium bromide occurred in a one-way manner.For example, methyl 5-O-benzyl-β-D-ribofuranoside (3β) was converted into the corresponding α-anomer (3α) in a 95p