4.4- Dideoxy-trehalose derivative

Enzymic methods were used to link a-D-glucopyranose to the anomeric positions of a-D-lyxopyranose and P-D-xylulose. Various dichloro-dideoxy sucroses and products derived by selective nucleophilic displacement of single chlorine atoms are referred to in Chapter 8. Trehalose derivatives carrying long-chain branched fatty acid residues are referred to in Chapter 19. 

Diazido-4,4 -dideoxy-ga/acto-trehalose was synthesized from a known partially benzoylated trehalose derivative by formation and azide ion displacement of a 4,4 -ditriflate, and was claimed to have antimicrobial properties. ... 

The trehalose derivatives 3-0-benzyl-4,6-0-benzylidene-2-deoxy-a-D-ri/>o-hexopyranosyl 4, 6 -0-benzylidene-2 -deoxy-a-D-rifto-hexopyranoside and 2,2, 3,3 -tetra-0-benzoyl-6,6 -dideoxy-4,4 -di-0-mesyl-6,6 -dithiocyanato-a,o-tre-halose di-iV-acetylchitobiose complexed to turkey egg lysozyme. ... 

Figure 16. Synthesis of 2-deoxy, 3-deoxy, and 23-dideoxy derivatives of a.a-trehalose.

The same behavior [38] was found for 6,6 -dideoxy-6,-6 -diisothiocyanato-Q ,a -trehalose 5 (Scheme 2), prepared by isothiocyanation of 4. Reactivity of fully-O-protected 6-deoxy-6-isothiocyanato derivatives with ammonia in several solvents to provide either thioureas or cyclic thiocarbamates has also been reported [39]. 

In the area of non-reducing disaccharides various 2-deoxy, 3-deoxy and 2,3-dideoxy derivatives of a,o-trehalose have been made by reductive desulphonylation of tosylates with lithium tri-ethylborohydride, and a bis-allo-2,3-epoxlde has afforded a route to 3-amino-3-deoxy-a-D-mannopyranosyl 3-amino-3-deoxy-a-D-... 

Two polymorphs of a,a-trehalose octacetate monohydrate, 4,4 -dideoxy-a,a- ty/o-trehalose, methyl 2,3,4,6,2, 4, 6 -hepta-C -acetyl-a-laminaribinoside, 2 3,3 -dideoxy-a,a-flrflbjno-trehalosc. 3 Methyl 2,3-0-isopropylidene-5-0-tosyl-P-D-ribofuranoside 2, the 7-carbon glycoside 3 (see Chapter 17), C-glycosidic furanoside 4 (see Chapter 14) the oxazoline derivative 5 and methyl 1,6-di-0-(4-bromobenzoyl)-3,4-di-0-(4-methoxycinnamoyl)-P-D-fructofuranoside. Di-(3-deoxy-D-g/yccro-pcntulose)-l,2 2,r-dianhydridc, methyl 4,6-benzylidene-a-D-allopyranoside, methyl-2,3,4-tri-0-acctyl-a-L-rhamnopyranoside, l 2-(indol-3-yl)ethyl 2,3,4-tri-O-acetyl-a-L-... 

Selective acid>catalysed methanolysis of 2,3,2, 3 -tetra-0-benzyl-4,6 4, 6 -di-0-benzylidene-a,a-trehalose gave the monoacetal which was converted into the dimesylate and from this 6-deoxy-6-fluoro-a,a-trehalose was obtained. In the course of the work 4-chloro-4,6-dideoxy-6-fluoro-a-D-galactopyranosyl a-D-glucopyranoside was produced (as a derivative), and 6-iodo, 6,6 -di-iodo, 6-azido-, and 6,6 -diazido-trehalose compounds were also prepared. 6-Deoxy-6-fluoro- and 6-deoxy-6-iodo-trehalose were also obtained by way of the... 

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