6,6 -dideoxy Sucrose

However, based on the following evidence, a question has been raised about the assumed Sn2 character of the displacement reaction.78 The reaction of 2,3,4,l, 3, 4 -hexa-0-benzoylsucrose 6,6 -bis(chlorosulfate) (44) with pyridinium chloride in chloroform for 4 h at 55° gave 2,3,4,l, 3, 4 -hexa-0-benzoyl-6,6 -dichloro-6,6 -dideoxy-sucrose (54) in 96% yield. When compound 44 was heated under reflux with butanone alone, compound 54 (35%) was the only iso-... 

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. 

A short synthesis of 3,4,6-tri-0-benzyl-l,5-dideoxy-l,5-imino-D-mannitol has been achieved by acid-catalysed hydrolysis, followed by controlled reductive amination of a per-benzylated l,6 -diazido-l,6 -dideoxy-sucrose derivative. Further transformation by way of an azide displacement of a 2-0-triflyl derivative afforded ultimately 2-acetamido-l,2,5-trideoxy-l,5-imino-D-glucitol (2-acet-amido-1,2-dideoxynojirimycin). ... 

Dideoxy-sucrose has been synthesized reglospecifically from sucrose by synthesis (2,2 -dipyridyldisulphide-Ph P) and reductive desulphurization (Raney Ni) of 6,6 -dldeoxy-6,6 -bis(2-pyridylthlo)... 

A crystalline 5,5 -diene, or bis (vinyl ether), derivative of sucrose has been prepared from 6,6 -dideoxy- 6,6 -diiodo-sucrose hexa-acetate, derived from the 6,6 -ditosylate, by treatment with silver fluoride in pyridine (26). 

Trichloro-4,6,6 -trideoxygalactosucrose or6-chloro-6-deoxy-p-D-fructofuranosyl 4,6-dichloro-4,6-dideoxy-a-D-galactopyranoside ( galactosucrose is a trivial name for the 4-epimer of sucrose)... 

Deoxy-4-fluoro- a/flc/o-sucrose (617 4-deoxy-4-fluoro-a-D-galacto-pyranosyl D-fructofuranoside), 2,3,1, 3, 4, 6 -hexa-0-benzyl-4,6-dideoxy-4,6-difluorosucrose (618), 2,3,1, 3, 4, 6 -hexa-0-benzyl-6-deoxy-6-... 

The Sn2 reaction of octa-0-(methylsulfonyl)sucrose with sodium bromide revealed further the comparative reactivities of the sulfonyloxy substituent at C-6, C-6, and other carbon atoms.97 On treatment with sodium bromide in butanone, octa-0-(methylsul-fonyl)sucrose gave 6,6 -dibromo-6,6 -dideoxy-2,3,4,l, 3, 4 -hexa-O-(methylsulfonyl)sucrose and an equimolar mixture of 6- and 6 -bromodeoxysucrose heptakis(methanesulfonates) in 21 and 61% yield, respectively. Unlike the conclusion from previous observations,29,96 presence of the latter product suggested that the reactivities of the 6- and 6 -sulfonyloxy substituents in octa-O-(methylsulfonyl)-sucrose are comparable. The evidence was based only on the results of measurement of the intensity peaks of the H n.m.r. spectra of the... 

Dideoxy-2,5-imino-D-mannitol 7 (Scheme 3) in complex (PDB 2AEY) with chicory fructan 1-exohydrolase (EC 3.2.1.153 GH 32) was found to bind in a similar way as does fructose, as well as the fructofuranosyl subunit of sucrose and... 

Sucralose, 1,6-dichloro-1,6-dideoxy-/3-o-fructofuranosyl 4-chloro-4-deoxy-o -D-galacto-pyra-noside or 4,1, 6 -trichloro-4,l, 6 -trideoxy-ga/acfo-sucrose (Fig. 1), is a chlorinated derivative of sucrose discovered in 1976 and marketed under the brand name Splenda . Its chemical formula is C 2H 908C13 (MW 397.35). It is a white, odorless, crystalline powder that is soluble in water (280 g/L at 20°C), methanol, and ethanol. Sucralose is 400-800 times sweeter than sucrose (Table 1). It has a clean, sugarlike taste and a time-intensity profile much like that of sucrose, although more persistent. It has no bitter or any other objectionable aftertaste. It is a flavor enhancer. It shows sweetness synergism with cyclamate, acesulfame-K, and neohesperidin dihy-drochalcone (8,25,57,86). 

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