13121-62-5

Upstream product

• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 154618-72-1 phenyl 2,3,4,6-tetra-O-acetyl-1-seleno-β-D-galactopyranoside 
• 134160-51-3 5-exo-(benzeneselenyl)-6-endo-chloro-3-methylidene-7-oxabicyclo<2.2.1>heptan-2-one 
• 141665-74-9 Fmoc-ΔAla-Phe-OBzl 
• 141665-76-1 Z-Pro-ΔAla-Ala-OBzl 
• 141665-73-8 Fmoc-ΔAla-OBzl 
• 94882-75-4 benzyl (2-t-butoxycarbonylamino)acrylate 
• 59524-07-1 N-(Benxyloxycarbonyl)dehydroalanine benzyl ester 
• 108-24-7 acetic anhydride 
• 99756-41-9 benzyl hepta-O-diethylboryl-β-lactoside 
• 96532-70-6 per-O-diethylboryl-D-lactose 
• 96532-71-7 C₄₄H₉₄B₈O₁₁ 

Downstream Products

• 3971-48-0 1,5-anhydro-D-galactitol 

Relevant academic research and scientific papers

NaBH3CN and other systems as substitutes of tin and silicon hydrides in the light or heat-initiated reduction of halosugars: A tunable access to either 2-deoxy sugars or 1,5-anhydro-itols

UV light-promoted reduction of acetobromoglucose by NaBH3CN in t-BuOH afforded 1,3,4,6-tetra-O-acetyl-2-deoxy-α-d-arabino-hexopyranose in high yield and purity, via a Surzur-Tanner rearrangement, while, with 10 mol % thiophenol added, acetylated 1,5-anhydro-d-glucitol was cleanly obtained. Such tin-free and mild reductions, presumed to proceed via radical pathways, were more efficient with NaBH3CN compared to NaBH4 or NaBD 4, and do not occur with acetochloroglucose. Similar reductions to 1,3,4,6-tetra-O-acetyl-2-deoxy-α-d-arabino-hexopyranose were achieved upon heating to 80 C t-BuOH or CH3CN solutions of NaBH3CN and AIBN, but with a lower selectivity due to competing ionic reactions. With other pyranosyl bromides, reductions by NaBH3CN could be tuned similarly (d-galacto), but some (d-manno, 5-thio-d-xylo) gave mainly or exclusively 1,5-anhydro-itols. Other conditions, or reagents promoting SET process, afforded also reduced products, but with lower rates or selectivities. Primary iodides were reduced readily with NaBH3CN under UV light.

Synthetic utility of 1,1,2,2-tetraaryIdisilanes: Radical reduction of alkyl phenyl chalcogenides

Reactivity of tetraaryldisilanes as radical reducing agents of alkyl phenyl chalcogenides initiated by Et3B or AIBN was studied. Here, the reactivity of alkyl sulfide was poor; however, various alkyl phenyl selenides and tellurides were reduced to the corresponding hydrocarbons in good yields with 1,1,2,2-tetraphenyldisilane. The Royal Society of Chemistry 1999.

Reductive Oxa Ring Opening of 7-Oxabicycloheptan-2-ones. Synthesis of C-α-Galactosides of Carbapentopyranoses

Photoinduced electron transfer from Et3N to 7-oxabicycloheptan-2-ones can generate the corresponding 3-hydroxycyclohexanone derivatives.The method has been applied to the synthesis of C-α-D-galactopyranosides of carbapentapyranoses.Radical α-D-gaactosidation of (+/-)- (1RS,4RS,5RS,6RS)-6-endo-methoxy-3-methylidene-5-exo-(phenylseleno)-7-oxabicyclohept-2-one ((+/-)/51) followed by seleno-Pummerer rearrangement and reduction with Bu3SnH gave (+)-(1R,2S,3S,4R,6S)-((+)-58) and (+)-(1S,2R,3R,4S,6S)-3-endo-methoxy-5-oxo-6-endo--7-oxabicyclo hept-2-endo-yl acetate ((+)-59), which were separated by column chromatography.Irradiation (254 nm) in the presence of Et3N gave (+)-(1S,2R,3R,6R)- ((+)-60) and (+)-(1R,2S,3S,6S)-2-hydroxy-6-methoxy-4-oxo-3-,(2',3',4',6'-tetra-O-acetyl-α-D-galactopyranosyl)methyl>cyclohexyl acetate (+)-61, respectively.NaBH4 reduction and acetylation provided (+)-(1S,2S,3R,4R,5R)- ((+()-62) and (+)-(1R,2R,3S,4S,5S)-5-methoxy-2-cyclohexa-1,3,4-triyl triaceate ((+)-64).

Synthesis of α-D-(13) and α-D-(14)-C-linked Galactosides of D-mannose Derivatives. Conformation of α-C-Galactosides.

Reductive radical α-D-galactosidation of 5-exo-(benzeneselenyl)-6-endo-chloro-3-methylidene-7-oxabicycloheptan-2-one with acetobromo-D-galactose, followed by ketone reduction led to (+)-(1R,2S,3R,4S,5S,6S)-5-exo-(benzeneselenyl)-6-endo-chloro-3-end

Unprecedented Influence of Azides and the Effect of Bulky Groups on Zinc-induced Reductions of Deoxy Halogeno Sugars

Zinc/silver-graphite induced ring-opening reactions of deoxy halogeno sugars by dealkoxyhalogenation may be suppressed by bulky protecting goups in the substrates, giving rise to simple dehalogenation products.Furanose derivatives are more sensitive to such steric effects than pyranose systems, although an X-ray analysis of 1,2-O-isopropylidene-3-O-benzyl-5-deoxy-5-iodo-α-D-xylofuranose 3 shows no evidence of steric hindrance by the C-3 substituent.Morever, dehalogenation instead of reductive ring-opening reactions are observed in all cases in which organic azides are present in the reaction medium.This unprecedented effect of azides on zinc-induced reductions is equally effective both intra- and intermolecularly.This behaviour is best rationalized by assuming radical intermediates for dehalogenations, in contrast to transient organometallic species closely bound to the zinc surface when reductive ring-opening is observed.This mechanistic interpretation is supported by a labelling experiment.