62641-00-3

Upstream product

• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 
• 79834-15-4 (2-bromo-3,5-bis(methoxymethoxy)phenyl)methanol 
• 67-66-3 chloroform 
• 82598-88-7 2,3,4,6-tetra-O-benzyl-D-mannono-1,5-lactone 
• 64-17-5 ethanol 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 362623-58-3 methyl 3-azido-3-deoxy-2,4,6-tri-O-benzyl-α-D-altro-hexopyranoside 
• 100-39-0 benzyl bromide 
• 20379-58-2 methyl 3-azido-3-deoxy-α-D-altropyranoside 

Downstream Products

• 16134-31-9 2.4.6-Tri-O-benzyl-3-desoxy-L-threo-hex-2-enopyranose 
• 16134-30-8 2,4,6-Tri-O-benzyl-3-desoxy-N,N-dimethyl-L-threo-hexen-2-onamid 

Relevant academic research and scientific papers

C-2 Epimerization of aldonolactones promoted by magnesium iodide: a new way towards non-enzymatic epimerization

The first example of a non-enzymatic C-2 epimerization of aldonolactones is reported. The reaction of 2,3,4,6-tetra-O-benzyl-d-gluconolactone or 2,3,4,6-tetra-O-benzyl-d-mannonolactone with MgI2 in EtOH afforded their respective C-2 epimer. Studies conducted in EtOD showing the incorporation of a deuterium atom only at the C-2 position of the epimerized product reveal an epimerization rather than a racemization reaction. A mechanism involving a chelation with a magnesium species is proposed to explain this C-2 inversion reaction.

The synthesis of carbohydrate α-amino acids utilizing the Corey-Link reaction

Various carbohydrate ketones (uloses) have been treated with chloroform under strongly basic conditions to yield trichloromethyl tertiary alcohols. These alcohols, when subjected to the conditions of the modified Corey-Link reaction (sodium azide and 1,8-

Preparation and reactivity of some 3-deoxy-D-altronic acid derivatives

3-Amino-3-deoxy-2,4,5,6-tetra-O-methyl-D-altronic acid hydrochloride was the key intermediate in the preparation of poly[(2S,3R)-2-methoxy-3-(D-erythro-trimethoxypropyl)propanamide], a chiral nylon 3 analog. We now describe an alternative synthetic route

Easy access to C-glycosides from aldonolactones by a Claisen-type chain-extension reaction

Chain elongated 2,4-diuloses 2, 4, 6, 9-11, 24, 25 were conveniently obtained from the corresponding aldonolactones 1, 3, 5 by their reaction with carbonyl compounds in the presence of sodium hydride. These hemiacetalic products can be transformed into C-

Synthesis of the papulacandin C-arylglucosyl spiroketal nucleus

The enantiomerically pure tricyclic C-arylglucosyl spiroketal nucleus of papulacandin has been synthesized by reaction of an appropriately protected gluconolactone 4 with a metalated derivative of 5-(hydroxymethyl)resorcinol (5). In model studies, alkylli

Highly Stereoselective Grignard Reaction of an Aldopyranose: A Simple Synthesis of 6-Deoxy-D-idose from D-Xylose

Grignard reaction of 2,3,4-tri-O-benzyl-D-xylopyranose yielded a single product with very high stereoselectivity.A threo relationship of the newly created chiral center with respect to C2 was established by converting the product into the δ-lactone of D-ido configuration, then to the unsaturated lactone of threo configuration.The result made possible a stereoselective synthesis of 6-deoxy-D-idose from D-xylose in a small number of steps.Models accounting for the high stereoselectivity in the Grignard reaction of aldoses are discussed.Keywords - Grignard reaction; stereoselectivity; configuration of unsaturated lactones; 2,3,4-tri-O-benzyl-D-xylose; 1-deoxy-D-sorbose; 6-deoxy-D-iono-1,5-lactone; 6-deoxy-D-idose; stereocontrol models