77388-95-5

Upstream product

• 71026-41-0 Hexadecanoic acid 2-((2R,3R,4S,5R,6R)-3,5-bis-benzyloxy-6-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-2-yloxy)-1-hexadecyloxymethyl-ethyl ester 
• 496877-70-4 (S)-N-α-benzyloxyacetyl-4-benzyl-5,5-dimethyloxazolidin-2-one 
• 496877-71-5 (2'S,3'R,4S)-4-benzyl-3-(2',4'-bis(benzyloxy)-3'-hydroxybutyryl)-5,5-dimethyloxazolidin-2-one 
• 496877-72-6 (2'S,3'R,4S)-4-benzyl-3-(2',4'-bis(benzyloxy)-3'-(tert-butyldimethylsilanyloxy)butyryl)-5,5-dimethyloxazolidin-2-one 
• 846542-07-2 (2'R,3'S,4R,4'R,5'R)-4-benzyl-3-[2',4',6'-tris(benzyloxy)-5'-(tert-butyldimethylsilanyloxy)-3'-hydroxyhexanoyl]-5,5-dimethyloxazolidin-2-one 
• 60656-87-3 benzyloxyacetoaldehyde 
• 77388-96-6 2,4,6-tri-O-benzyl-α-D-glucopyranosyl chloride 
• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 350254-95-4 3-O-allyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 89068-02-0 allyl 3-O-allyl-β-D-glucopyranose 
• 77388-92-2 allyl 2,4,6-tri-O-benzyl-3-O-(1-propenyl)-α-D-glucopyranose 
• 100-44-7 benzyl chloride 
• 48149-74-2 allyl D-glucopyranoside 
• 2280-44-6 D-Glucose 

Downstream Products

• 10257-28-0 D-Galactose 
• 912650-98-7 2,4,6-tri-O-benzyl-D-glucono-1,5-lactone 
• 89104-67-6 1,3-di-O-acetyl-2,4,6-tri-O-benzyl-β-D-glucopyranose 
• 77388-97-7 1,5-anhydro-2,4,6-tri-O-benzyl-D-arabino-hex-1-enitol 
• 33208-48-9 1,6 anhydro-2,4-di-O-benzyl-β-D-glucopyranose 
• 89068-05-3 3-O-acetyl-2,4,6-tri-O-benzyl-α-D-glucopyranosyl chloride 
• 76543-11-8 1,3-anhydro-2,4,6-tri-O-benzyl-β-D-glucopyranose 
• 912650-48-7 3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-manno-hept-2-ulosyl-(2->3)-2,4,6-tri-O-benzyl-D-glucono-1,5-lactone 
• 912650-45-4 3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-galacto-hept-2-ulosyl-(2->3)-2,4,6-tri-O-benzyl-D-glucono-1,5-lactone 
• 912650-42-1 3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-hept-2-ulosyl-(2->3)-2,4,6-tri-O-benzyl-D-glucono-1,5-lactone 
• 77388-96-6 2,4,6-tri-O-benzyl-α-D-glucopyranosyl chloride 
• 889361-05-1 (N-phenyl)trifluoroacetimidoyl 2,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 77448-40-9 Acetic acid (2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-bromo-tetrahydro-pyran-4-yl ester 
• 77364-20-6 methyl 2,4,6-tri-O-benzyl-β-D-mannopyranoside 

Relevant academic research and scientific papers

Synthesis of helicobacter-pylorus O2 serotype O antigen oligosaccharide compound

The invention discloses discloses synthesis of a helicobacter-pylorus O2 serotype O antigen oligosaccharide compound, and belongs to the field of organic synthesis. According to the synthesis, helicobacter-pylorus O2 serotype O-antigen disaccharide to tet

Sequential one-pot glycosidations catalytically promoted: Unprecedented strategy in oligosaccharide synthesis for the straightforward assemblage of the antitumor PI-88 pentasaccharide

(Chemical Equation Presented) The pentasaccharide sequence of the most active components of the antitumor drug PI-88, currently in phase II clinical trial, has been rapidly assembled in high overall yield and in only three steps starting from three monosa

Synthesis of 1-deoxyhept-2-ulosyl-glycono-1,5-lactone utilizing α-selective O-glycosidation of 2,6-anhydro-1-deoxy-d-hept-1-enitols

A series of 1-deoxy-heptulo-2-pyranosyl-glycono-1,5-lactones were synthesized utilizing completely α-selective O-glycosidation of heptenitols. Anomeric configuration of the products was confirmed by 3JC,H coupling measurement and X-ray crystal structural analysis. The benzyl-protected ketosyl saccharides were partly unstable, and glycosidic linkage was prone to cleave under the usual debenzylation conditions. To prevent this, we surveyed various additives for the Pd-catalyzed hydrogenation reaction and found that basic alumina was the most effective.

Amino acid catalyzed neogenesis of carbohydrates: A plausible ancient transformation

Hexose sugars play a fundamental role in vital biochemical processes and their biosynthesis is achieved through enzyme-catalyzed pathways. Herein we disclose the ability of amino acids to catalyze the asymmetric neogenesis of carbohydrates by sequential cross-aldol reactions. The amino acids mediate the asymmetric de novo synthesis of natural L- and D-hexoses and their analogues with excellent stereoselectivity in organic solvents. In some cases, the four new stereocenters are assembled with almost absolute stereocontrol. The unique feature of these results is that, when an amino acid is employed as the catalyst, a single reaction sequence can convert a protected glycol aldehyde into a hexose in one step. For example, proline and its derivatives catalyze the asymmetric neogenesis of allose with > 99% ee in one chemical manipulation. Furthermore, all amino acids tested catalyzed the asymmetric formation of natural sugars under prebiotic conditions, with alanine being the smallest catalyst. The inherent simplicity of this catalytic process suggests that a catalytic prebiotic "gluconeogenesis" may occur, in which amino acids transfer their stereochemical information to sugars. In addition, the amino acid catalyzed stereoselective sequential cross-aldol reactions were performed as a two-step procedure with different aldehydes as acceptors and nucleophiles. The employment of two different amino acids as catalysts for the iterative direct aldol reactions enabled the asymmetric synthesis of deoxysugars with > 99% ee. In addition, the direct amino acid catalyzed C2+C 2+C2 methodology is a new entry for the short, highly enantioselective de novo synthesis of carbohydrate derivatives, isotope-labeled sugars, and polyketide natural products. The one-pot asymmetric de novo syntheses of deoxy and polyketide carbohydrates involved a novel dynamic kinetic asymmetric transformation (DYKAT) mediated by an amino acid.

Plausible origins of homochirality in the amino acid catalyzed neogenesis of carbohydrates

The intrinsic ability of amino acids to catalyze the asymmetric formation of carbohydrates, which enzymes have mediated for millions of years, with significant amplification of enantiomeric excess suggests a plausible ancient catalytic process for the evo

A SuperQuat glycolate aldol approach to the asymmetric synthesis of hexose monosaccharides

A stereoselective two-carbon homologation protocol has been developed and applied to the asymmetric synthesis of the hexose monosaccharides D-galactose, D-fucose, D-idose, D-6-deoxyidose, D-talose and D-6-deoxytalose.

Direct amino acid catalyzed asymmetric synthesis of polyketide sugars

Back to the future: In a biomimetic asymmetric synthesis of sugars (see scheme) sequential cross-aldol reactions of simple aldehydes were catalyzed by amino acids. Deoxysugars were obtained with excellent chemoselectivity and up to > 99% ee. This transfor

Preparation of an advanced intermediate for the synthesis of stable analogues of guanofosfocin

The synthesis of C-mannosyl-guanosine 23, an advanced intermediate for the preparation of stable analogues of guanofosfocin, is described. This convergent approach features an improved Traube-type synthesis of a 8-substituted guanine, followed by ribosylation. NMR Studies show that the C-mannopyranosyl moiety of 23 adopts a distorted 1C4 conformation while the nucleoside is predominantly syn-oriented.

DIRECT, ENANTIOSELECTIVE ALDOL COUPLING OF ALDEHYDES USING CHIRAL ORGANIC CATALYSTS

Nonmetallic, chiral organic catalysts are used to catalyze an enantioselective aldol coupling reaction between aldehyde substrates. The reaction may be carried out with a single enolizable aldehyde, resulting in dimerization to give a β-hydroxy aldehyde,

The asymmetric synthesis of D-galactose via an iterative syn-glycolate aldol strategy

The asymmetric synthesis of D-galactose has been completed in eight steps and in >14% yield from simple starting materials via an iterative syn-glycolate aldol strategy.