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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| Abstract | 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. |
|---|---|
| AbstractList | 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. 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. |
| Abstract_FL | On présente deux méthodes de préparation du chlorure d'hexa-O-acetyl-déoxy-2-phtalimido-2-β-
D
-lactosyle (
7
) à partir de l'hexaacétate de lactale (
1
). Une méthode fait intervenir, dans la première étape, la réaction du composé
1
avec le chlorure de nitrosyle et passe par un intermédiaire benzylamino-2-déoxy-2-α-
D
-lactoside (
4
). L'autre méthode, que l'on considère plus efficace, fait intervenir la réaction de
1
avec le nitrate d'ammonium cérique et l'azoture de sodium et implique comme intermédiaire l'anomère β (
12
) du composé
4
. L'intérêt de la préparation du composé
7
réside dans le fait qu'il est un moyen d'accès aux amino-2-déoxy-2-β-
D
-lactosides. Les méthodes ouvrent la voie à la préparation de la
D
-lactosamine.[Traduit par le journal] |
| Author | Abbas, S. Z Ratcliffe, R. M Burzynska, M. H Lemieux, R. U |
| Author_xml | – sequence: 1 givenname: R. U surname: Lemieux fullname: Lemieux, R. U – sequence: 2 givenname: S. Z surname: Abbas fullname: Abbas, S. Z – sequence: 3 givenname: M. H surname: Burzynska fullname: Burzynska, M. H – sequence: 4 givenname: R. M surname: Ratcliffe fullname: Ratcliffe, R. M |
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| Snippet | 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... 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... |
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| Title | Syntheses of derivatives of N-acetyl-D-lactosamine from D-lactal hexaacetate. Hexa-O-acetyl-2-deoxy-2-phthalimido-β-D-lactosyl chloride |
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