91780-41-5

Upstream product

• 119-61-9 benzophenone 
• 91780-35-7 3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl chloride 
• 630-19-3 pivalaldehyde 
• 123-72-8 butyraldehyde 
• 66-25-1 hexanal 
• 78-84-2 isobutyraldehyde 
• 120-92-3 cyclopentanone 
• 96-22-0 pentan-3-one 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 64978-34-3 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranosyl sulfone 
• 62774-37-2 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glucopyranoside 
• 64978-35-4 1,5-anhydro-3,4,6-tri-O-benzyl-1,2-dideoxy-1-phenylsulfonyl-D-arabino-hex-1-enitol 
• 139974-82-6 2-methylpropane-2-yl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-glucopyranoside 

Relevant academic research and scientific papers

Reduction of olefins using ruthenium carbene catalysts and silanes

Ruthenium carbene complexes are able to mediate reduction of olefins in the presence of trialkylsilanes. Under these reduction conditions, when kinetically favorable ring-closing metathesis is possible, a one-pot cyclization-reduction sequence can be performed. Georg Thieme Verlag Stuttgart.

A single-process desulfonylation of perbenzylated-α- and -β-D-glycopyranosyl phenyl (tert-butyl)sulfones

Phenyl and/or tert-butyl α or β-D-glucopyranosyl sulfones were treated with lithium aluminum hydride and potassium hydroxide respectively to afford conveniently desulfonylated products (4 and 5). From the former reductive process was isolated the 2-deoxy-

SmI2-promoted chemistry at the anomeric center of carbohydrates. Reductive formation and reaction of glycosyl samarium (III) reagents

Reaction of 3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranosyl chloride at room temperature with the efficient single electron transfer system of SmI2-THF-HMPA, in the presence of cyclopentanone (Barbier conditions) gave selectively the corresponding α-C-glycoside in 70percent yield.It is postulated that the reactive transient intermediate is a chiral anomeric organosamarium (III) species.Lower yields were obtained in the presence of aldehydes, such as n-butanal or isobutanal.It is also demonstrated that glycosyl phenyl sulfones undergo reductive samariation. 2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl phenyl sulfone reacted with cyclopentanone, in the presence of SmI2-THF-HMPA, to give the corresponding β-C-glycoside selectively in 25percent yield, together with the elimination product (40percent).When the protecting group at C-2 was an acetate, a very fast β-elimination of the organosamarium intermediate occurred to give a practically quantitative yield of a substituted glycal.This work constitutes the first application of samarium(II) iodide to the reductive metallation of the anomeric center of carbohydrates.Key words: samarium diiodide / sulfones / carbohydrates / glycals / C-glycosides

Stereospecific Generation of α- and β-Glycosyl-lithium Reagents from Glycosyl-stannanes: a Stereocontrolled Route to α- and β-C-Glycosides

Treatment of α- and β-D-tri-n-butylstannyl-glucopyranosides with n-butyl-lithium at -78 deg C generates configurationally stable α- and β-D-glycosyl-lithium species which accept electrophiles with retention of configuration.

Simple Generation of a Reactive Glycosyl-lithium Derivative

Two-step hydrolithiation of 3,4,6-tri-O-benzyl-D-glucal (hydrochlorination and lithium naphthalenide reductive lithiation) gives a reactive glycosyl-lithium derivative which is shown to be a precursor of C-glycosides.