Acetyl migration in partially acetylated D-glucopyranosides and acylamidohexopyranosides

Rainer Albert; Karl Dax; Arnold Stütz; Hans Weidmann

doi:10.1080/07328308308057874

Acetyl migration in partially acetylated D-glucopyranosides and acylamidohexopyranosides

Rainer Albert, Karl Dax, Arnold Stütz, Hans Weidmann

Institute of Organic Chemistry (6410)

Research output: Contribution to journal › Article › peer-review

Abstract

0-4—0-6 Acetyl migrations in partially O-acetylated 2- and 3-acylamidodeoxyhexopyranosides, including derivatives of kanamycin A, were found to be particularly suited to allow the regiospecific accessibility of their respective C-4 OH groups. Partially O-acety-lated D-glucopyranosides, compared to the substrates above, showed slightly different aptitudes of migration. However, all 0-4-0-6 migrations investigated proved to be irreversible under the conditions applied.

Original language	English
Pages (from-to)	279-299
Journal	Journal of Carbohydrate Chemistry
Volume	2
Issue number	3
DOIs	https://doi.org/10.1080/07328308308057874
Publication status	Published - 1983

Access to Document

10.1080/07328308308057874

Glycochemistry and Glycotechnology
Wrodnigg, T. (Co-Investigator (CoI)), Stütz, A. (Principal Investigator (PI)) & Steiner, A. (Co-Investigator (CoI))
1/01/88 → 31/01/23
Project: Research area

Cite this

@article{9828f71174a5406787bd57b3df971e03,

title = "Acetyl migration in partially acetylated D-glucopyranosides and acylamidohexopyranosides",

abstract = "0-4—0-6 Acetyl migrations in partially O-acetylated 2- and 3-acylamidodeoxyhexopyranosides, including derivatives of kanamycin A, were found to be particularly suited to allow the regiospecific accessibility of their respective C-4 OH groups. Partially O-acety-lated D-glucopyranosides, compared to the substrates above, showed slightly different aptitudes of migration. However, all 0-4-0-6 migrations investigated proved to be irreversible under the conditions applied.",

author = "Rainer Albert and Karl Dax and Arnold St{\"u}tz and Hans Weidmann",

year = "1983",

doi = "10.1080/07328308308057874",

language = "English",

volume = "2",

pages = "279--299",

journal = "Journal of Carbohydrate Chemistry",

issn = "1532-2327",

publisher = "Taylor and Francis Ltd.",

number = "3",

}

TY - JOUR

T1 - Acetyl migration in partially acetylated D-glucopyranosides and acylamidohexopyranosides

AU - Albert, Rainer

AU - Dax, Karl

AU - Stütz, Arnold

AU - Weidmann, Hans

PY - 1983

Y1 - 1983

N2 - 0-4—0-6 Acetyl migrations in partially O-acetylated 2- and 3-acylamidodeoxyhexopyranosides, including derivatives of kanamycin A, were found to be particularly suited to allow the regiospecific accessibility of their respective C-4 OH groups. Partially O-acety-lated D-glucopyranosides, compared to the substrates above, showed slightly different aptitudes of migration. However, all 0-4-0-6 migrations investigated proved to be irreversible under the conditions applied.

AB - 0-4—0-6 Acetyl migrations in partially O-acetylated 2- and 3-acylamidodeoxyhexopyranosides, including derivatives of kanamycin A, were found to be particularly suited to allow the regiospecific accessibility of their respective C-4 OH groups. Partially O-acety-lated D-glucopyranosides, compared to the substrates above, showed slightly different aptitudes of migration. However, all 0-4-0-6 migrations investigated proved to be irreversible under the conditions applied.

U2 - 10.1080/07328308308057874

DO - 10.1080/07328308308057874

M3 - Article

SN - 1532-2327

VL - 2

SP - 279

EP - 299

JO - Journal of Carbohydrate Chemistry

JF - Journal of Carbohydrate Chemistry

IS - 3

ER -

Acetyl migration in partially acetylated D-glucopyranosides and acylamidohexopyranosides

Abstract

Access to Document

Fingerprint

Projects

Glycochemistry and Glycotechnology

Cite this