2-amino-2-deoxy-glycosides

Scheme 5.56 Routes to 2-amino-2-deoxy-glycosides from glycals.

A reaction which is analogous to the orthoester synthesis but which utilises glycosyl oxazolines affords means of synthesising, 2-trans-2 amino-2-deoxy-glycoside derivatives. Treatment of the gluco compomd (17) with phenol in the presence of toluene- -sulphonic acid thus gave the glycoside (18), and it was also utilised in a nucleoside synthesis 48). 

Pentenyl 2-Amino-2-Deoxy Glycoside Derivatives as Glycosyl Donors. 583... 

Buten-2-yl 2-amino-2-deoxy Glycosides as Glycosyl Donors. 625... 

Several pent-4-enyl 2-amino-2-deoxy glycoside derivatives were evaluated as glycosyl donors for the synthesis of 2-amino-2-deoxy oligosaccharides [64], 2-Deoxy-2-phthalimido 96, and 2-anisylimino-2-deoxy-D-glucop)Tanosides 98, underwent IDCP-induced coupling with... 

Mootoo DR, Fraser-Reid B (1989) Pentenyl 2-amino-2-deoxy glycosides undergo... 

Full details have been published on the [4+2]cyclo-addition of dibenzyl azodicarboxylate to O-silylated glycals, and the conversion of the adducts to 1,2-trans-related 2-amino-2-deoxy-glycosides by reaction with alcohol in the presence of an acid catalyst (c Vol.22, p.97). By using bis(trichloroethyl) azodicarboi late, this route has now been extended for use with acetylated... 

A new method for the preparation of 2-amino-2-deoxy-glycosides involved the cycloaddition of dibenzyl azodicarboxylate to glycals. Puranoid and pyranoid glycals, (23) and (2M), gave single cycloadducts (25) and (26) which methanolysed with inversion at C-1 to provide glycosides (27) and (28), respectively (Schemes 5 and 6). 

A new method for preparing 2-amino-2-deoxy glycosides is illustrated in Scheme 1 and can be applied with furanoid derivatives... 

Seeberger et al., 1997 Lehmann, 1976, 1996). Glycals are versatile synthetic intermediates in the synthesis of 2-deoxy- and 2-amino-glycosides (see Scheme 4.4.5) (Fraser-Reid, 1975 Fraser-Reid and Anderson, 1980). Reaction of glycal and alcohol in the presence of promoters (Ag+/1, NBS) and subsequent reductive dehalogenation (Hj-Pd, Bu SnH-AiBN) produces preferentially the 2-deoxy-(-glycoside. 

Synthetic approaches to anthracycline antibiotics have been reviewed. Several papers report syntheses of daunorubicin analogues by the glycosidation of daunomycinone derivatives with amino-sugars glycosides of daunomycinone have been prepared from 3-epf-L-daunosamine, D-acosamine, D-daunosamine, D-ristosamine, and 3-ep(-D-daunosamine, and 4-demethoxy-9-deoxy-9-methyl... 

A series of pseudo-disaccharides has been prepared by condensing appropriate deoxy-inositol and glycal derivatives to give a-linked 3 -deoxy-cyclitol glycosides, e.g. (29) which were further transformed to amino-deoxy-cyclitol glycosides, e.g. (30). ... 

Synthesis of amino-sugar glycosides is covered in Chapter 3, the formation of 2-acetamido-2-deoxy-D-glucosides from diazirines via glycosyl carbenes in Chapter 10, and the conversion of a deoxynojirimycin derivative into 2,6-dideoxy-2,6-imino-L-gulonic acid in Chapter 18. 

Syntheses of amino-sugar glycosides and disaccharides, including chromogenic substrates for A -acetyl-p-D-glucosaminidase, are covered in Chapter 3. Synthesis of protected 2-amino-2-deoxy-glycosyl azides is covered in Chapter 10. 2,3,6-Trideoxy-5-0-(4-nitrobenzoyl)-3-trifluoroacetamido-L-riho-hexofuranosyl bromide, a furanoid ristosamine derivative, was synthesized from L-rhamnal via intermediates reported previously (Vol.25, p.253) to effect glycosylations. ... 

The generic term monosaccharide (as opposed to oligosaccharide or polysaccharide) denotes a single unit, without glycosidic connection to other such units. It includes aldoses, dialdoses, aldoketoses, ketoses and diketoses, as well as deoxy sugars and amino sugars, and their derivatives, provided that the parent compound has a (potential) carbonyl gTOup. 

Scheme 2. — Nitrous Acid Deamination of 2-Amino-2-deoxy-D-glucose and Its Glycosides.

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