439914-99-5

Upstream product

• 151669-25-9 Phenyl 2,3-O-isopropylidene-6-O-(p-toluenesulfonyl)-1-thio-α-D-mannopyranoside 
• 1207976-08-6 phenyl 1-thio-α-D-rhamnopyranoside 
• 104-15-4 toluene-4-sulfonic acid 
• 77-76-9 2,2-dimethoxy-propane 
• 151669-24-8 Phenyl 6-O-(p-toluenesulfonyl)-1-thio-α-D-mannopyranoside 
• 2936-70-1 (2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 256327-73-8 Toluene-4-sulfonic acid (3aS,4R,6R,7R,7aR)-2,2-dimethyl-4-phenylsulfanyl-7-triisopropylsilanyloxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl ester 

Downstream Products

• 848693-47-0 Phenyl 4-O-benzyl-2,3-O-isopropylidene-1-thio-α-D-rhamnopyranoside 
• 151669-28-2 Phenyl 4-O-benzyl-2-O-methyl-1-thio-α-D-rhamnopyranoside 
• 1207976-08-6 phenyl 1-thio-α-D-rhamnopyranoside 
• 439915-02-3 Thiocarbonic acid O-[(2R,3R,4S,5R,6S)-3-benzyloxy-2-methyl-5-phenylsulfanyl-6-((3aS,4R,6R,7R,7aS)-2,2,6-trimethyl-4-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy)-tetrahydro-pyran-4-yl] ester S-methyl ester 
• 439915-00-1 Phenyl 4-O-benzyl-1-thio-α-D-rhamnopyranoside 
• 896436-02-5 (2R,3R,4S,5S,6R)-4-Allyloxy-3-methoxy-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran 
• 896435-93-1 (2R,3S,4R,5R,6R)-4-Allyloxy-5-methoxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol 
• 896435-87-3 (2R,3S,4R,5S,6R)-5-Methoxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3,4-diol 
• 896435-80-6 (3aS,4R,6R,7R,7aS)-7-Methoxy-2,2,6-trimethyl-4-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran 

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

Synthesis of (-)-sordarin

The first total synthesis of (-)-sordarin (1) was accomplished exploiting the following key reactions: (i) Ag(I)-catalyzed oxidative radical cyclization of a cyclopropanol derivative leading to a bicyclo-[5.3.0]decan-3-one skeleton; (ii) Pd(0)-catalyzed i

Synthesis of p-trifluoroacetamidophenyl 6-deoxy-2-O--α-L-rhamnopyranosyl>-α-L-talopyranoside: a spacer armed tetrasaccharide glycopeptidolipid antigen of Mycobacterium avium serovar 2

The synthesis of the title tetrasaccharide glycoside 38 is reported. p-Nitrophenyl endo-3,4-O-benzylidene-6-deoxy-α-L-talopyranoside (4), 3-O-acetyl-2,4-di-O-benzyl-α-L-rhamnopyranosyl trichloroacetimidate (7), methyl 3-O-acetyl-4-O-benzyl-2-O-methyl-1-th