637771-89-2

Upstream product

• 135395-53-8 C₆H₁₀NO₇P^(2-) 
• 209786-19-6 Methanesulfonic acid (R)-1-{(4S,5R)-5-[(R)-1-tert-butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethyl ester 
• 1037306-48-1 (2R,3R,4R,5S)-3,4-bis(benzyloxy)-2-(hydroxymethyl)-5-methylpyrrolidine 
• 944544-02-9 (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-methylpyrrolidine 
• 1037306-55-0 (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(hydroxymethyl)-5-methylpyrrolidine 
• 944543-92-4 (2R,3R,4R,5R)-3,4-dihydroxy-2-(hydroxymethyl)-5-methylpyrrolidine hydrochloride 
• 1310481-39-0 C₁₄H₁₉NO₆ 
• 1274764-32-7 C₁₄H₁₉NO₆ 
• 1037306-51-6 (2R,3S,4R,5R)-3,4-bis(benzyloxy)-1-(tert-butoxycarbonyl)-2-(hydroxymethyl)-5-methylpyrrolidine 
• 17102-64-6 Sorbyl alcohol 
• 1274764-14-5 (3R,4S,5S)-PhCH₂OC(O)NHCH(Me)CH(OH)CH(OH)C(O)CH₂OH 
• 1037673-62-3 (2R,3R,4S,5S)-3,4-dibenzyloxy-2-hydroxymethyl-5-methylpyrrolidine 
• 264234-48-2 2,5-(benzyloxycarbonylimino)-3,4-O-isopropylidene-2,5,6-trideoxy-D-talose 

Relevant academic research and scientific papers

Catalytic Regio- and Enantioselective Haloazidation of Allylic Alcohols

Herein we report a highly regio- and stereoselective haloazidation of allylic alcohols. This enantioselective reaction uses readily available materials and can be performed on a variety of alkyl-substituted alkenes and can incorporate either bromine or chlorine as the electrophilic halogen component. Both halide and azido groups of the resulting products can be transformed into valuable building blocks with complete stereospecificity. The first example of an enantioselective 1,4-haloazidation of a conjugated diene is reported as well as its application to a concise synthesis of an aza-sugar.

Hanessian-Hullar reaction in the synthesis of highly substituted trans-3,4-dihydroxypyrrolidines: Rhamnulose iminosugar mimics inhibit α-glucosidase

The key step in the syntheses of highly substituted trans-3,4-dihydroxypyrrolidines is introduction of bromide by stereospecific and regiospecific Hanessian-Hullar reactions; benzylidene lactones of L-rhamnonolactone and 6-deoxy-this should be small unnpercase D not L why can I not correct this-gulonolactone allow introduction of N at C2 with inversion or retention of configuration. Initially a protecting group, the benzylidene acetal then provides a bromide at C5 to allow formation of the pyrrolidine ring. With silyl protecting groups, bromide was introduced at C5 with inversion of configuration whereas benzoyl protection gave a mixture of retention and inversion, indicative of neighbouring group participation in a Hanessian-Hullar reaction. Four stereoisomeric pyrrolidines - iminosugar mimics of α- and β-L-rhamnulose and α- and β-6-deoxy-D-sorbose were prepared. Only the α-L-rhamnulose mimic showed moderate inhibition of rhamnosidase but some were good inhibitors of α-glucosidases; none inhibited rhamnose isomerase and they had a small effect as synthetic inducers of the rhamnose catabolic operon in E. coli.

Synthesis of di- and trihydroxy proline derivatives from D-glycals: Application in the synthesis of polysubstituted pyrrolizidines and bioactive 1C-aryl/alkyl pyrrolidines

Six different types of O-benzyl protected proline derivatives have been synthesized from D-glycals and 2C-formyl-glycals. One of the di-O-benzyl protected proline derivatives has been utilized for the synthesis of polysubstituted pyrrolizidines via [3 + 2

L -Rhamnulose-1-phosphate Aldolase from Thermotoga maritima in Organic Synthesis: One-Pot Multistep Reactions for the Preparation of Imino- and Nitrocyclitols

Rhamnulose-1-phosphate aldolase from Thermotoga maritima (Rhu1PATm) has been recently cloned and characterised. This hyperthermophilic enzyme offers intriguing possibilities for practical catalysis. This is due to its high stability under extreme reaction

Sugar-derived cyclic imines: One-pot synthesis and direct functionalization

A simple method for the synthesis of sugar-derived imines by a Schwartz's reagent reduction of easily available sugar lactams has been described. A direct addition of nucleophiles to the generated in situ cyclic imines and subsequent deprotection of hydroxyl function allows to convert sugar lactams in polyhydroxylated pyrrolidines and piperidines.

Structure-guided redesign of d-fructose-6-phosphate aldolase from E. coli: Remarkable activity and selectivity towards acceptor substrates by two-point mutation

Structure-guided re-design of the acceptor binding site of d-fructose-6-phosphate aldolase from E. coli leads to the construction of FSA A129S/A165G double mutant with an activity between 5- to >900-fold higher than that of wild-type towards N-Cbz-aminoal

Redesign of the phosphate binding site of L -rhamnulose- 1-phosphate aldolase towards a dihydroxyacetone dependent aldolase

The aldol addition of unphosphorylated dihydroxyacetone (DHA) to aldehydes catalyzed by L-rhamnulose-1-phosphate aldolase (RhuA), a dihydroxyacetone phosphate-dependent aldolase, is reported. Moreover, a single point mutation in the phosphate binding site

Diversity-oriented synthesis of useful chiral building blocks from D-mannitol

A diversity-oriented synthesis is described for functionalized chiral building blocks (i.e., 7, 9, 10, 16, and 17) and the biologically active iminosugar, fucosidase inhibitor (2S,3R,4R,5R)-2-(hydroxymethyl)-5- methylpyrrolidine-3,4-diol (22), starting fr

Lipase-mediated synthesis of enantiomeric 2,5,6-trideoxy-2,5-iminohexitols

Syntheses of 2,5,6-trideoxy-2,5-imino-d-alditol (2, 6-deoxy-DADP) and its enantiomer (3) from tri-orthogonally protected derivatives of DADP have been developed employing lipase-mediated kinetic desymmetrization and protecting group manipulations. Thus, and as an example, the starting DADP derivative (4) was transformed into a new symmetrical 2,5-bis(hydroxymethyl)pyrrolidine (6) by sequential N-protection and bis-O-desilylation. The lipase-mediated desymmetrization of 6 was best carried out under acetylation conditions to give (2R)-acetyloxymethyl derivative 7. The absolute configuration and ee of 7 were unambiguously established by chemical correlation with a homochiral sample. Compound 7 was straightforwardly transformed into the target 2,5,6-trideoxy-2,5-iminohexitol 3.

Polyhydroxylated pyrrolidines: Synthesis of trideoxy-2,5-iminohexitols

A series of naturally occurring pyrrolidine alkaloids and analogues, with the general structure of trideoxy-2,5-iminohexitols (imino- or azasugars), have been enantiosynthesized using triorthogonally protected pyrrolidines, previously prepared from commercial D-fructose, as homochiral starting materials. The inhibitory activity of some of the described compounds against glycosidases and glycosyltransferases makes them potential therapeutic agents. Georg Thieme Verlag Stuttgart.