85716-44-5

Upstream product

• 85716-43-4 methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 59578-04-0 methyl 2,3,4-tri-O-trimethylsilyl-6-deoxy-6-iodo-α-D-glucopyranoside 
• 20771-10-2 1-O-methyl-2,3,4-tri-O-trimethylsilyl-α-D-glucopyranoside 
• 2595-06-4 methyl 2,3,4-tri-O-benzyl-6-O-trityl-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 116386-41-5 (3S,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-methylene-tetrahydro-pyran-3-ol 
• 7177-79-9 methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 4356-80-3 methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 73111-13-4 Methanesulfonic acid (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester 
• 18311-26-7 methyl 6-O-trityl-α-D-glucopyranoside 
• 6984-65-2 methyl 2,3,4-tri-O-trimethylsilyl-5-methylene-α-D-xylopyranoside 
• 6304-96-7 methyl 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-α-D-glucopyranoside 

Downstream Products

• 85716-45-6 1L-(2,4,5/3)-2,3,4-Tri-O-benzyl-2,3,4,5-tetrahydroxy-1-cyclohexanon 
• 87984-31-4 (2S,3R,4S,5R) 5-hydroxy-2,3,4-tris(benzyloxy) cyclohexane-1-one 
• 85798-11-4 (4S,5R,6S)-4,5,6-tris-benzyloxycyclohex-2-en-1-one 
• 606930-14-7 (2S,3R,4S)-2,3,4-tris-benzyloxy-5-hydroxycyclohexan-1-one 
• 189222-28-4 (1S,2S,3S,4R,5R)-2,3,4-tri-O-benzyl-1-O-methylcyclohexane-1,2,3,4,5-pentol 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 205192-05-8 methyl 2,3,4-tri-O-benzyl-β-L-idopyranoside 
• 208333-61-3 (2S,3R,4S,5S)-2,3,4-Tris-benzyloxy-5-methoxy-cyclohexanone 
• 243980-62-3 (5R,7S,8R,9R,10S)-8,9,10-Tris(benzyloxy)-7-methoxy-3-(4-methylphenyl)-1,6-dioxa-2-azaspiro[4.5]dec-2-ene 
• 316172-35-7 2,3,4-tri-O-benzyl-1,6-anhydro-β-L-idopyranos-5-ulo-5-hydrate 
• 439614-74-1 (3S,5S,6R,7R,8S)-6,7,8-Tris-benzyloxy-5-methoxy-1,4-dioxa-spiro[2.5]octane 
• 641635-63-4 ((3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-methanol 

Relevant academic research and scientific papers

Carbocyclic Substrate Analogues Reveal Kanosamine Biosynthesis Begins with the α-Anomer of Glucose 6-Phosphate

NtdC is an NAD-dependent dehydrogenase that catalyzes the conversion of glucose 6-phosphate (G6P) to 3-oxo-glucose 6-phosphate (3oG6P), the first step in kanosamine biosynthesis in Bacillus subtilis and other closely-related bacteria. The NtdC-catalyzed r

Stereoselective Synthesis of C, C-Glycosides from exo-Glycals Enabled by Iron-Mediated Hydrogen Atom Transfer

We describe herein a convenient strategy for the construction of C,C-glycoside building blocks via the intermediacy of tertiary pseudoanomeric radicals. Application of an iron-mediated hydrogen atom transfer/Michael-Giese coupling enables the anomeric quaternization of readily available exo-glycals with good to complete stereocontrol in the pyranose and furanose series. Carefully optimized conditions allow the use of challenging trisubstituted derivatives prone to undergo further elaboration to stable neoglycoconjugates. Preliminary results for direct C-disaccharide synthesis are also discussed.

Vinyl Grignard-Mediated Stereoselective Carbocyclization of Lactone Acetals

A novel Ferrier-type carbocyclization is reported. It involves a carbohydrate-derived lactone acetal synthesized from methyl α-d-glucopyranoside, which upon treatment with excess vinylmagnesium bromide provides a highly substituted carbocyclic product as a single stereoisomer. The yield is greatly increased when N,N,N′,N′-tetramethylethylenediamine is added to the reaction mixture. Optimized reaction conditions have been applied to lactone acetals derived from other carbohydrates. Based on the obtained results, a possible reaction mechanism has been proposed. Furthermore, scalability of the reaction up to 15 g scale and derivatization of the carbocyclic product has been demonstrated, including the formation of a rare trans-bicyclo[4.3.0]nonene scaffold via a ring-closing metathesis. The structure of this and all carbocyclic products were confirmed by X-ray crystallographic analysis.

Stereoselective synthesis of 1,6-dioxaspirolactones from spiro-cyclopropanecarboxylated sugars: Total synthesis of dihydro-pyrenolide D

An efficient method for the stereoselective construction of 1,6-dioxaspiro[4.n]decan-2-one systems (n = 4, 5) from sugar derived spirocyclopropane carboxylic acids involving a one-pot ring-opening and cyclization reaction is revealed. The generality of th

Conformational Plasticity in Glycomimetics: Fluorocarbamethyl- L -idopyranosides Mimic the Intrinsic Dynamic Behaviour of Natural Idose Rings

Sugar function, structure and dynamics are intricately correlated. Ring flexibility is intrinsically related to biological activity; actually plasticity in L-iduronic rings modulates their interactions with biological receptors. However, the access to the

Syntheses of (-)-gabosine A, (+)-4-epi-gabosine A, (-)-gabosine E, and (+)-4-epi-gabosine e

(+)-4-epi-Gabosine A 1 and (-)-gabosine A 2 have been synthesized starting from methyl α,d-glucopyranoside and methyl α,d-mannopyranoside, respectively, by utilizing Pd(0) catalyzed Stille coupling as the key step. On the other hand, syntheses of (+)-4-ep

Do upper limits to the multiple spiro acetalization of the cyclohexane ring exist?

An attempt to transform the pyranoside (5) into the bifaciai ligand (3) is described. The first subtarget is acetal (13) whose conversion into tris acetal (17) is made possible by remote C-H activation. Regrettably, triol (20) does not lend itself to comparable triple cyclization.

Surprising bacterial nucleotidyltransferase selectivity in the conversion of carbaglucose-1-phosphate

The drive to understand the molecular determinants of carbohydrate binding as well as the search for more chemically and biochemically stable sugar derivatives and carbohydrate-based therapeutics has led to the synthesis of a variety of analogues that rep

Facile generation of alkenes and dienes from tosylates

Several aldol products resulting from Evans aldol reactions were converted to primary alcohols. After conversion to the corresponding tosylates, heating with NaI and DBU in dimethoxyethane (glyme) effected clean elimination to the terminal olefin. This simple one-pot procedure was applied to other tosylates and a tosylate derived from a homoallylic alcohol. The latter gave rise to a diene.

A study of the epoxidation of 6-deoxyhex-5-enopyranosides. 1,5-Dicarbonyl derivatives and novel synthetic routes to D-xylo-hexos-5-ulose and D-lyxo-hexos-5-ulose

The work described deals with the isolation and characterization of epoxides from 6-deoxyhex-5-enopyranosides and preliminary exploration of their synthetic potential. Prolonged epoxidation reaction times led to their hydrolysis in situ and gave novel protected D-hexos-5-ulose derivatives (sugar 1,5-dicarbonyls). Some reactions of the hexos-5-uloses were studied, and in some cases septanoside (seven-membered-ring saccharide) derivatives were isolated. Novel routes to D-xylohexos-5-ulose and D-lyxo-hexos-5-ulose, of interest as intermediates in the synthesis and biosynthesis of inositols and aza sugars, are also described. The structures of the epoxides and novel hexos-5-uloses were established by NMR and X-ray crystallographic methods.