76951-87-6

Upstream product

• 83051-83-6 1,2:3,4-Di-O-isopropylidene-6-N-((carbobenzyloxy)amino)-6-deoxy-7-O-acetyl-L-glycero-α-D-galacto-heptopyranose 
• 501-53-1 benzyl chloroformate 
• 161377-15-7 (S)-2-Amino-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethanol 
• 67-64-1 acetone 
• 321658-31-5 (R)-3-(benzyloxycarbonyl)-2,2-dimethyl-4-<(E)-2-carbomethoxyvinyl>oxazolidine 
• 147455-56-9 6-(Benzyloxycarbonylamino)-6-deoxy-1,2:3,4-di-O-isopropylidene-β-L-glycero-D-galacto-heptodialdo-1,5-pyranose 
• 138312-57-9 1,2:3,4-Di-O-isopropylidene-6-(N-(benzyloxycarbonyl)amino)-6-deoxy-7-O-(tert-butyldiphenylsilyl)-L-glycero-α-D-galacto-heptopyranose 
• 138286-60-9 2(R)-<1'(S)-((Benzyloxycarbonyl)amino)-2'-((tert-butyldiphenylsilyl)oxy)ethyl>-3(S)-(benzyloxy)-4(R)-hydroxy-2,3-dihydro-4H-pyran 
• 122051-28-9 2(R)-<1'(S)-((Benzyloxycarbonyl)amino)-2'-((tert-butyldiphenylsilyl)oxy)ethyl>-3(S)-(benzoyloxy)-2,3-dihydro-4H-pyran-4-one 
• 135245-97-5 methyl (2S)-3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)-2-[(phenylmethoxy)carbonylamino]propanoate 
• 122051-27-8 N-(Benzyloxycarbonyl)-O-(tert-butyldiphenylsilyl)-L-serinal 
• 76951-82-1 1,2:3,4-di-O-isopropylidene-6-O-(methylsulfonyl)-α-D-glycero-D-galacto-heptopyranurononitrile 
• 76951-84-3 (S)-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-aziridine 
• 19342-68-8 Hydroxy-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-acetonitrile 

Downstream Products

• 83051-83-6 1,2:3,4-Di-O-isopropylidene-6-N-((carbobenzyloxy)amino)-6-deoxy-7-O-acetyl-L-glycero-α-D-galacto-heptopyranose 

Relevant academic research and scientific papers

Stereoselective synthesis of differentially protected derivatives of the higher amino sugars destomic acid and lincosamine from serine and threonine

The aminoheptose destomic acid (3.5) and the aminooctose lincosamine (6.8) were synthesized in protected form by parallel sequences starting from the oxazolidine derivatives 2.4 and 5.1 of N-CBz serinal and N-BOC threoninal. The parallel sequences feature

Stereoselective Homologation-Amination of Aldehydes by Addition of Their Nitrones to C-2 Metalated Thiazoles - A General Entry to α-Amino Aldehydes and Amino Sugars

A general method for the homologation of aldehydes to α-amino aldehydes (aminohomologation) has been developed, which employs nitrones as iminium derivatives of the aldehydes.Key operations include a) the addition of a thiazole metalated at C-2 to the N-benzylnitrone derived from the aldehyde, b) the reductive dehydroxylation of the resultant thiazolyl N-benzylhydroxylamine, and c) the unmasking of the formyl group from the thiazole ring.The homologation sequence was studied by employing nitrones derived from various chiral polyalkoxy aldehydes and dialdoses.The addition of 2-lithiothiazole to these nitrones was syn-selective, whereas the reaction with the same nitrones precomplexed with Lewis acids was anti-selective.Hence, from each nitrone a pair of diastereoisomeric hydroxylamines was obtained.These compounds were then converted by the above sequence into α-epimeric α-amino aldehydes.Model elaborations of some of these products afforded the amino sugars D-glucosamine, D-mannosamine, D-nojirimycin, and advanced intermediates for the synthesis of destomic acid and lincosamine. - Keywords: amino aldehydes; aminohomologation; amino sugars; nitrones; thiazoles

Stereocontrolled Hydroxymethylation of Carbohydrate Imines: Formal Synthesis of Destomic Acid and Lincosamine

Addition of magnesium chloride to 6-benzylimino-6-deoxy-1,2;3,4-di-O-isopropylidene-α-D-galactopyranose mediated by Ce(III)Cl3 or CuI/BF3*Et2O proceeds with complete syn- or anti-diastereoselectivity, respectively, to afford h

SYNTHESIS OF DESTOMIC AND epi-DESTOMIC ACID, AND THEIR C-6 EPIMERS

Four stereoisomers of 6-amino-6-deoxyheptonic acid, having the L-glycero-D-galacto (1), D-glycero-D-galacto (2), L-glycero-D-gluco (3), and D-glycero-D-gluco(4) configurations, were synthesized from D-galacto- (8) and D-gluco-dialdose (23) derivatives, respectively.Cyanomesylation of 8 and 23 gave two C-6 epimers, respectively, which were separately converted, via the corresponding 6,7-epimino derivatives, into 6-(benzyloxycarbonyl)amino-6-deoxy derivatives by reduction with lithium aluminium hydride, N-(benzyloxycarbonyl)ation, and acetolysis with acetic acid.After deprotection of each hemiacetal, the stereoisomers were oxidized with bromine, followed by total deprotection, to give 1-4.Among these products, 1 and 3 proved to be identical with the naturally occuring destomic and epi-destomic acid obtained from antibiotic destomycins.

SYNTHESIS OF DESTOMIC ACID AND ITS 6-EPIMER

The structure of 6-aminoheptonic acid component contained in destomycin A and C was confirmed first by chemical synthesis.