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Formation of the butylidene acetas of α-chloralose
The acid-catalysed reaction of α-chloralose 1 ( 1, 1,2- O-trichloroethylidene-α- d-glucofuranose, the isomer having m.p. 190-195°) with butyraldehyde gave two stereoisomeric, crystalline 5,6- O-butylidene-1,2- O-trichloroethylidene-α- d-glucofuranoses ( 2 and 3). The structures of 2 and 3 were ident...
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| Published in: | Carbohydrate research 1977, Vol.56 (1), p.87-91 |
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| Main Author: | |
| Format: | Article |
| Language: | English |
| Citations: | Items that this one cites Items that cite this one |
| Online Access: | Get full text |
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| Summary: | The acid-catalysed reaction of α-chloralose
1 (
1, 1,2-
O-trichloroethylidene-α-
d-glucofuranose, the isomer having m.p. 190-195°) with butyraldehyde gave two stereoisomeric, crystalline 5,6-
O-butylidene-1,2-
O-trichloroethylidene-α-
d-glucofuranoses (
2 and
3). The structures of
2 and
3 were identified by chemical and spectroscopic means. The formation of the 3,5-acetal(
11) was not observed in the direct butylidenation of α-chloralose, but
11 could be synthesised by indirect routes. The butylidene acetal ring of
11 was hydrolysed much more readily than the butylidene group of
2 or
3. |
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| ISSN: | 0008-6215 1873-426X |
| DOI: | 10.1016/S0008-6215(00)84239-1 |