73861-92-4

Upstream product

• 197567-94-5 (2S,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-methyl-piperidine-2-sulfonic acid 
• 1000855-27-5 C₁₄H₁₉NO₆ 
• 17682-70-1 2,3:4,6-bis-O-isopropylidene-L-sorbose 
• 195380-93-9 1,5-imino-1,5,6-trideoxy-N-benzhydryl-2,3,4-tri-O-benzyl-D-glucitol 
• 144848-60-2 (3aS,3bR,7aS,8aR)-8a-Fluoromethyl-2,2,5,5-tetramethyl-tetrahydro-[1,3]dioxolo[4,5]furo[3,2-d][1,3]dioxine 
• 144848-59-9 Trifluoro-methanesulfonic acid (3aS,3bR,7aS,8aS)-2,2,5,5-tetramethyl-tetrahydro-[1,3]dioxolo[4,5]furo[3,2-d][1,3]dioxin-8a-ylmethyl ester 
• 144848-62-4 Toluene-4-sulfonic acid (3aR,5S,6R,6aS)-3a-fluoromethyl-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester 
• 144848-63-5 (3aR,5S,6R,6aS)-5-Azidomethyl-3a-fluoromethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol 
• 144848-61-3 (3aR,5S,6R,6aS)-3a-Fluoromethyl-5-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol 
• 1429471-03-3 benzyl (5S)-5-[(1S,2S)-1,2-dihydroxy-3-oxobutyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 197567-82-1 (3R,4R,5S,6R)-6-Dimethoxymethyl-4,5-dihydroxy-3-methyl-[1,2]oxazinane-2-carboxylic acid benzyl ester 
• 173829-12-4 (3R,4R,5R,6R)-6-Dimethoxymethyl-4,5-dihydroxy-3-methyl-[1,2]oxazinane-2-carboxylic acid benzyl ester 
• 314252-29-4 2,3,4-tri-O-acetyl-5-amino-5,6-dideoxy-D-glucono-1,5-lactam 
• 17682-71-2 2,3-O-isopropylidene-α-L-sorbofuranose 

Relevant academic research and scientific papers

Organocatalytic syn-aldol reactions of hydroxy ketones with (S)-isoserinal: Asymmetric synthesis of 6-deoxy-1,5-iminohexitols and related compounds

An improved and convenient preparation of protected (S)-isoserinal on a large scale is reported. This key intermediate was reacted through organocatalyzed aldol reaction or Wittig based chain extension and functionalization to give enantiopure 1,5,6-trideoxy-1,5-imino-hexitols such as 10a (L-manno) and 10b (D-gluco). These two compounds are of interest as glycosidase inhibitors. The elaborated organocatalytic process includes diastereoselective syn aldol reaction of (S)-isoserinal hydrate and hydroxyacetone or 1-hydroxy-2-octanone and is promoted by various amino acid-based catalysts. Diastereoselectivities of up to 8:1 were achieved, thus establishing a new, efficient synthetic route to these important carbohydrate mimics. A novel protocol for the preparation of 1,5,6-trideoxy-1,5-imino-L- mannitol and 1,5,6-trideoxy-1,5-imino-D-glucitol is reported. The key steps include organocatalyzed syn-selective direct aldol reaction of hydroxyacetone and CBz-protected isoserinal hydrate, followed by reductive amination/ cyclization. Copyright

D-fructose-6-phosphate aldolase-catalyzed one-pot synthesis of iminocyclitols

A one-pot chemoenzymatic method for the synthesis of a variety of new iminocyclitols from readily available, non-phosphorylated donor substrates has been developed. The method utilizes the recently discovered fructose-6-phosphate aldolase (FSA), which is functionally distinct from known aldolases in its tolerance of different donor substrates as well as acceptor substrates. Kinetic studies were performed with dihydroxyacetone (DHA), the presumed endogenous substrate for FSA, as well as hydroxy acetone (HA) and 1-hydroxy-2-butanone (HB) as donor substrates, in each case using glyceraldehyde-3-phosphate as acceptor substrate. Remarkably, FSA used the three donor substrates with equal efficiency, with kcat/KM-values of 33, 75, and 20 M -1 s-1, respectively. This level of donor substrate tolerance is unprecedented for an aldolase. Furthermore, DHA, HA, and HB were accepted as donors in FSA-catalyzed aldol reactions with a variety of azido- and Cbz-amino aldehyde acceptors. The broad substrate tolerance of FSA and the ability to circumvent the need for phosphorylated substrates allowed for one-pot synthesis of a number of known and novel iminocyclitols in good yields, and in a very concise fashion. New iminocyclitols were assayed as inhibitors against a panel of glycosidases. Compounds 15 and 16 were specific α-mannosidase inhibitors, and 24 and 26 were potent and selective inhibitors of β-N-acetylglucosaminidases in the submicromolar range. Facile access to these compounds makes them attractive core structures for further inhibitor optimization.

A facile synthesis of 1,6-dideoxynojirimycin from l-sorbose

A practical synthesis of 1,6-dideoxynojirimycin, a potent glycosidase inhibitor, starting from l-sorbose, is described.

A general approach to the synthesis of dideoxy and trideoxyiminoalditols from β-D-glycosides

Imino sugars (also called azasugars), a class of compounds of which the 1,5-dideoxy and 1,5,6-trideoxyiminoalditols are members, are important glycosidase inhibitors with very high potential as drugs. Their potential therapeutic applications range from the treatment of diabetes to cancer and AIDS. We present here a general method for the preparation of such compounds with the D-gluco and D-galacto configurations starting from β-D-glycosides. The procedure is especially appealing because of its high stereoselectivity and straightforwardness. The key steps are the selective oxidation of the glycosides to hexulosonic acids and reduction of the oxime derivatives to lactams, which are further reduced to the target compounds. The C-6 position can be deoxygenated during the reduction if it bears an acetoxy group. Trideoxy imino sugars are then produced. Deacetylation prior to oxime reduction gives dideoxy compounds. (C) 2000 Elsevier Science Ltd.

6-Deoxy-nojirimycin and 6-deoxy-gulo-nojirimycin in the racemic and D-series, D-fuco-nojirimycin and their 1-deoxyderivatives via hetero-Diels-Alder cycloadditions

Nucleophilic ring opening of the cyclic sulfates (±)-9c and D-9c and of the epoxide (±)-13, or double substitution of the bis-triflate D-10 (derived from the Diels-Alder adduct of hexodienal dimethylacetal to achiral or enantiomerically pure nitroso-derivatives) led to 6-deoxy-nojirimycin and 6-deoxy-gulo-nojirimycin in the racemic and D-series, to D-fuco-nojirimycin and to their 1-deoxyderivatives via their crystalline 1-deoxy-1-sulfonic acid derivatives (sulfite adducts). 6-Deoxy-nojirimycin and its isomers are mixtures of α- and β-anomers and of the corresponding imine.

Synthesis of 1,6-dideoxynojirimycin, 1,6-dideoxy-D-allo-nojirimycin, and 1,6-dideoxy-D-gulo-nojirimycin via asymmetric hetero-Diels-Alder reactions

Asymmetric Diels-Alder reaction of sorbaldehyde O-methyloxime 1d with chiral chloronitroso derivative 2 of D-mannose, followed by osmylation of the primary cycloadduct, led to diol 6a with excellent enantioselectivity (ee > 99%). Catalytic hydrogenolysis

Fluorinated 1,5-Dideoxy-1,5-iminoalditols: Synthesis of 1,5,6-Trideoxy-6-fluoro-1,5-imino-D-glucitol (1,6-Dideoxy-6-fluoronojirimycin) and 1,4,5-Trideoxy-4-fluoro-1,5-imino-D-ribitol (1,2,5-Trideoxy-2-fluoro-1,5-imino-L-ribitol)

An efficient synthesis of 1,5,6-trideoxy-6-fluoro-1,5-imino-D-glucitol 13 from inexpensive L-sorbose by way of reductive amination of 12 is described.Synthesis of 1,4,5-trideoxy-4-fluoro-1,5-imino-D-ribitol (1,2,5-trideoxy-2-fluoro-1,5-imino-L-ribitol) 19

Enzyme-catalyzed aldol condensation for asymmetric synthesis of azasugars: Synthesis, evaluation, and modeling of glycosidase inhibitors

A combined fructose 1,6-diphosphate aldolase reaction and catalytic reductive amination has been used in the asymmetric synthesis of azasugars structurally corresponding to N-acetylglucosamine, N-acetylmannosamine, and deoxyhexoses. The 6-deoxyazasugars w