126108-10-9

Upstream product

• 24850-33-7 allyltributylstanane 
• 66537-92-6 2-methoxy-6-phenyl-1a,2,3a,4-tetrahydrooxireno<4,5>pyrano<3,2-d><1,3>dioxin 
• 135759-86-3 methyl 4,6-O-benzylidene-2-deoxy-2-C-propenyl-α-D-arabino-hexopyranosid-3-ulose 
• 2622-05-1 allylmagnesium bromide 
• 66537-92-6 methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside 
• 109010-30-2 methyl 2-O-benzyl-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose 
• 141115-76-6 methyl 2-O-benzyl-4,6-O-(R)-benzylidene-α-D-arabinohexopyranosid-3-ulose 

Downstream Products

• 131529-43-6 methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-(prop-2-enyl)-α-D-altropyranoside 
• 131529-57-2 methyl 4,6-O-benzylidene-3-O-t-butyldimethylsilyl-2-deoxy-2-C-(prop-2-enyl)-α-D-altroside 
• 135759-86-3 methyl 4,6-O-benzylidene-2-deoxy-2-C-propenyl-α-D-arabino-hexopyranosid-3-ulose 
• 110087-69-9 2,2-Dimethyl-propionic acid (S)-6-benzyloxy-4-((4S,5R,6S)-6-hydroxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hexyl ester 
• 110099-22-4 2,2-Dimethyl-propionic acid (S)-6-benzyloxy-4-[(4S,5S,6R)-6-(2-hydroxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-hexyl ester 
• 110087-70-2 2,2-Dimethyl-propionic acid (S)-6-benzyloxy-4-((4S,5S,6R)-2,2,5-trimethyl-6-vinyl-[1,3]dioxan-4-yl)-hexyl ester 
• 110087-57-5 2,2-Dimethyl-propionic acid (S)-6-benzyloxy-4-((4S,5R,6S)-6-formyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hexyl ester 
• 110087-59-7 Toluene-4-sulfonic acid (2S,3R)-3-[(2R,3S,5R)-3-(bis-ethylsulfanyl-methyl)-5-methyl-6-oxo-tetrahydro-pyran-2-yl]-2-hydroxy-butyl ester 
• 110087-68-8 2,2-Dimethyl-propionic acid (S)-6-benzyloxy-4-[(4S,5R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-hexyl ester 
• 131529-50-5 methyl 3-O-benzyl-2-deoxy-2-C-(2-methoxycarbonylethyl)-6-O-phenylsulfonyl-α-D-altropyranoside 
• 131529-61-8 methyl 4-O-benzoyl-3-O-t-butyldimethylsilyl-6-cyano-2,6-dideoxy-2-C-(2-methoxycarbonylethyl)-α-D-altroside 
• 131529-28-7 methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-(2-methoxycarbonylpropyl)-α-D-altroside 
• 131529-60-7 methyl 4-O-benzoyl-6-bromo-3-O-t-butyldimethylsilyl-2,6-dideoxy-2-C-(2-methoxycarbonylethyl)-α-D-altroside 
• 131529-42-5 methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-(2-methoxycarbonylethyl)-α-D-altroside 

Relevant academic research and scientific papers

The stereoselective preparation of an enantiomerically pure cyclopentane using intramolecular aldol cyclopentaannulation of a glucose derivative

Methods for the annulation of carbohydrates have found extensive applications in organic synthesis. We report here a new protocol for the stereoselective conversion of glucose into an enantiomerically pure cyclopentane aldehyde 22. The readily available epoxide 15 was reacted with allyl Grignard to produce alcohol 16 in 86% yield. Swern oxidation followed by epimerization using triethylamine in N,N-dimethylformamide furnished the ketone 17 also in 86% yield. Regioselective deprotonation with lithium hexamethyldisilazane in THF was followed by methylation with methyl iodide and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone as cosolvent to give 80% yield of ketone 18. Oxidation of ketone 18 by the Wacker procedure gave the 1,4-diketone 19 in 56% yield. Intramolecular aldol condensation occurred readily on treatment of diketone 19 with potassium tert-butoxide in toluene to furnish a 90% yield of enone 20. Treatment with N-bromosuccinimide produced the bromoester 21 in 72% yield, which was reduced to a mixture of aldehydes 22 (61%) and 23 (14%) with zinc shot in 2-propanol.

Free Radical Substitutions of Acyloxy Groups in Carbohydrate α-Ketoesters

A range of carbohydrate derivatives containing α-ketoester functionality undergo efficient reductive loss of the acyloxy groups when treated with tri-n-butyltin hydride in refluxing benzene and in the presence of azoisobutyronitrile (AIBN) as radical init

The Synthesis of Some Carbohydrate-Derived Precursors to Tylonolide, the Aglycon of the Antibiotic Tylosin

Treatment of methyl 2,3-anhydro-4,6-O-benzylidene-α-D-alloside with the anion derived from trimethyl(prop-1-ynyl)silane, allylmagnesium chloride or isobutenylmagnesium chloride introduces a three- or four-carbon substituent at C2 of the sugar.In each case

SYNTHETIC STUDIES RELATING TO THE C1-C9 "EASTERN" HALF OF ROSARAMICIN

A pyranodisic homologation approach to the "eastern half" of rosaramicin is described.The synthetic plan calls for two one-carbon chain extensions, but these occur at "off-template" sites where asymmetric centers are neither destroyed nor created.However,