Syntheses of derivatives of N-acetyl-D-lactosamine from D-lactal hexaacetate. Hexa-O-acetyl-2-deoxy-2-phthalimido-β-D-lactosyl chloride
Two reaction routes are presented for the preparation of hexa-O-acetyl-2-deoxy-2-phthalimido-β- D -lactosyl chloride ( 7 ) from lactal hexaacetate ( 1 ). One route involves, in the first stage, reaction of 1 with nitrosyl chloride and proceeds by way of benzyl 2-amino-2-deoxy-α- D -lactoside ( 4 ) a...
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| Published in | Canadian journal of chemistry Vol. 60; no. 1; pp. 63 - 67 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
Ottawa, Canada
NRC Research Press
01.01.1982
|
| Online Access | Get full text |
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| Summary: | Two reaction routes are presented for the preparation of hexa-O-acetyl-2-deoxy-2-phthalimido-β-
D
-lactosyl chloride (
7
) from lactal hexaacetate (
1
). One route involves, in the first stage, reaction of
1
with nitrosyl chloride and proceeds by way of benzyl 2-amino-2-deoxy-α-
D
-lactoside (
4
) as an intermediate. The other route, which is considered more efficient, involves reaction of
1
with cerie ammonium nitrate and sodium azide and involves the β-anomer (
12
) of
4
as an intermediate. The preparation of
7
is of interest as a reagent for the preparation of 2-amino-2-deoxy-β-
D
-lactosides. The procedures offer routes for the preparation of
D
-lactosamine. |
|---|---|
| ISSN: | 0008-4042 1480-3291 |
| DOI: | 10.1139/v82-011 |