Dianhydro-D-sorbitol

Arlitan was treated with p-toluenesulfonyl chloride, followed by acetic anhydride, in pyridine solution and the tosyltriacetylanhydro-D-sorbitol so obtained was then treated with sodium methoxide. The product of the reaction was l,4 3,6-dianhydro-D-sorbitol. Accordingly,... 

Chloro-6-desoxy-3,5-benzylidene-l,4-anhydro-D-sorbitol (XVI) possesses an unusual property in that the benzylidene group is removed by distillation in alkaline or neutral solution. From the neutral solution it was possible to isolate 6-chloro-6-desoxy-l,4-anhydro-D-sorbitol as its triacetyl derivative. At the same time diacetyl-1,4 3,6-dianhydro-D-sorbitol was also formed. This removal of an acetal residue from a... 

Sorbitol forms a crystalline dianhydride, namely isosorbide this in contrast to isomannide was not described fully until recent times. Montgomery and Wiggins61 fully described it in 1946 but other authors had referred to it previously. In 1927 Muller and Hoffman62 described a liquid dianhydro-D-sorbitol which was probably an impure form of isosorbide. In 1940, Bell, Carr and Krantz63 described experiments with a crystalline dianhydro-D-sorbitol. Montgomery and Wiggins61... 

The rings in l,4 3,6-dianhydro-D-sorbitol have different stabilities. Montgomery and Wiggins66 treated the anhydride with hydrochloric acid under pressure and isolated some l,6-dichloro-l,6-didesoxy-D-sorbitol and much 6-chloro-6-desoxy-l,4-anhydro-D-sorbitol, both isolated as their benzylidene derivatives. No l-chloro-l-desoxy-3,6-anhydro-D-sorbitol was found. This experiment demonstrates that the 1,4-anhydro ring is more stable than the 3,6-ring in this substance. This is in agreement with the fact that partial dehydration of D-sorbitol in the 1,4-position can be preferentially effected and 1,4-anhydro-D-sorbitol isolated. 

Dianhydro-D-sorbitol (L-gulitol). 4. 2,5 Imino-2,5-didesoxy-l,4 3,6-dianhy-dro-D-mannitol. 

Fig. 2. Phenyl-2,3 4,6-tetra-0-bis(4-vinylphenylboronyl)-a-D-mannopyranoside 1, phenyl-a-D-mannopyranoside 2, EGDMA 3, TRIM 4, and 2,5-di-0-methacryloyl-l,4 3,6-dianhydro-D-sorbitol 5...

Cyclization of sorbitol in suitable conditions results in the formation of the 4,8-dihydroxy-c -2,6-dioxa-bicyclo[3.3.0]octane, also known as 1,4 3,6-dianhydro-D-sorbitol or Isosorbide (Figure 9.2.17). 

The 5-mononltrate of 1,4 3,6-dianhydro-D-sorbitol (1.e. isosor-bide), an active metabolite of the vasodilator isosorbide 2,5-... 

Fig.20. A Isosorbide (l,4 3,6-dianhydro-D-sorbitol). B Isomannide (1,4 3,6-dianhydro-D-mannitol). C Isoidide l,4 3,6-dianhydro-L-iditol (isoidide). Reprinted from (2002) Eur Polym J 38 1851 [87] with permission...

Eurthermore, elastomeric PUs with flexible degradability were prepared with PCL, HDI, and varying chain extenders [46,47]. Specifically, three new PUs, PU-S, PU-M, and PU-F, with bioactive isosorbidediol (l,4 3,6-dianhydro-D-sorbitol) (ISO), bis(2-mercaptoethyl) ether, and ISO combined with 3,7,1 l-trimethyl-2,6,10-dodecatrien-l-diaminobutane amide (TDD), respectively, used as chain extenders were synthesized [46,47]. These chain extenders acted as labile units and introduced different levels of polymer chain mobility into the polymeric materials [46]. 

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