Epimerisation of carbohydrates and cyclitols, 15 - Non-classical epimerisation of (1S,2S,3S,4R,5R)-1-O-methylcyclohexane-1,2,3,4,5-pentol | Health & Environmental Research Online (HERO)

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Tags

HERO ID

5340704

Reference Type

Journal Article

Title

Epimerisation of carbohydrates and cyclitols, 15 - Non-classical epimerisation of (1S,2S,3S,4R,5R)-1-O-methylcyclohexane-1,2,3,4,5-pentol

Author(s)

Frank, M; Miethchen, R; Reinke, H

Year

1999

Is Peer Reviewed?

Yes

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X
EISSN: 1099-0690

Issue

Page Numbers

1259-1263

DOI

10.1002/(sici)1099-0690(199905)1999:5<1259::aid-ejoc1259>3.0.co;2-n

Web of Science Id

WOS:000080228100035

URL

https://www.scopus.com/inward/record.uri?eid=2-s2.0-0032809181&doi=10.1002%2f%28sici%291099-0690%28199905%291999%3a5%3c1259%3a%3aaid-ejoc1259%3e3.0.co%3b2-n&partnerID=40&md5=4434dec6e2515dc501243efc262e15ca
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Abstract

Methoxycyclitol 4 was acetalized in a non-classical one-pot procedure with chloral/dicyclohexylcarbodiimide forming the 4-epi derivative 6. The stepwise deprotection of compound 6 is also described. Thus, decarbamoylation to the acetal 7 was achieved by heating 6 with methanolic sodium methoxide, and cleavage of the acid-stable trichloroethylidene moiety was realised in two steps via the corresponding ethylidene acetals 8 and 9; the ethylidene function was removed with aqueous trifluoroacetic acid (compound 10 from 6 via 9). Finally, the carbamoyl derivative 10 was converted into the tetra-O- acetyl product 12 via the tetrol 11.

Keywords

inositols; epimerisation; acetals; carbohydrates