848693-47-0

Upstream product

• 100-39-0 benzyl bromide 
• 439914-99-5 Phenyl 2,3-O-isopropylidene-1-thio-α-D-rhamnopyranoside 
• 151669-25-9 Phenyl 2,3-O-isopropylidene-6-O-(p-toluenesulfonyl)-1-thio-α-D-mannopyranoside 
• 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 

Downstream Products

• 151669-28-2 Phenyl 4-O-benzyl-2-O-methyl-1-thio-α-D-rhamnopyranoside 
• 439915-04-5 Thiocarbonic acid O-[(2R,3R,4S,5R,6S)-3-((2S,3R,4S,5S,6R)-5-benzyloxy-4-hydroxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-2-yloxy)-6-(4-methoxy-phenoxy)-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-4-yl] ester S-methyl ester 
• 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 
• 439915-03-4 Acetic acid (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 
• 439914-96-2 Acetic acid (2R,3R,4S,5R,6S)-3-benzyloxy-2-methyl-6-((3aS,4R,6R,7R,7aS)-6-methyl-4-phenylsulfanyl-2-thioxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy)-5-phenylsulfanyl-tetrahydro-pyran-4-yl ester 
• 439915-09-0 (2R,3S,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-ol 
• 439915-01-2 phenyl 4-O-benzyl-2,3-O-thionocarbonyl-1-thio-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

Efficient Synthesis of the Hexasaccharide Fragment of Landomycin A: Using Phenyl 2,3-O-Thionocarbonyl-1-thioglycosides as 2-Deoxy-β-glycoside Precursors

(Equation Presented) The β-p-methoxyphenol hexadeoxysaccharide fragment of landomycin A was synthesized in a total of 33 steps and 0.5% overall yield starting from D-mannose and D-xylose, featuring the use of phenyl 2,3-O-thionocarbonyl-1-thioglycosides a

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