1207976-08-6

Upstream product

• 439914-99-5 Phenyl 2,3-O-isopropylidene-1-thio-α-D-rhamnopyranoside 
• 1207976-11-1 C₁₂H₁₅IO₄S 
• 151669-24-8 Phenyl 6-O-(p-toluenesulfonyl)-1-thio-α-D-mannopyranoside 

Downstream Products

• 1191241-20-9 C₁₈H₂₂O₇S 
• 439914-99-5 Phenyl 2,3-O-isopropylidene-1-thio-α-D-rhamnopyranoside 

Relevant academic research and scientific papers

Synthesis of furanoid and pyranoid C-1 aryl glycals by reaction of glycosyl chlorides with organolithium reagents

Furanosyl and pyranosyl chlorides react with aryllithium derivatives, obtained by directed ortho-lithiation of activated arenes, to give C-1 aryl glycals in moderate yields.

Synthesis of orthogonally protected d-olivoside, 1,3-di-O-acetyl-4-O-benzyl-2,6-dideoxy-d-arabinopyranose, as a C-glycosyl donor

1,3-Di-O-acetyl-4-O-benzyl-2,6-dideoxy-d-arabinopyranose (11) was synthesised from thiophenyl α-d-mannopyranoside (21) in an eight-step sequence. Tosylation of 21 and subsequent reaction with 2,2-dimethoxypropane gave tosylate 22, which upon treatment with lithium aluminium hydride furnished 6-deoxy glycoside 24 and by-product thiophenyl 6-deoxy-2-O-isopropyl-α-d-arabinopyranoside. The X-ray crystal structure of the latter was determined. Benzylation of the 4-hydroxyl group of 24 and subsequent protecting group manipulation gave d-rhamnosyl bromide 29, which on treatment with zinc-copper couple gave the orthogonally protected d-rhamnal 30. Triphenylphosphine hydrogen bromide catalysed addition of acetic acid to 30 furnished the target molecule 11. The scandium(III) triflate promoted reaction of 11 and 2-naphthol gave the corresponding C-glycoside 36 in 86% yield. Crown Copyright