THE REPLACEMENT OF SECONDARY HYDROXYL GROUPS BY SULFONIC ACID SUBSTITUENTS

LESTER. YODER

doi:10.1021/jo01127a003

Preparation of prednisolone‐appended α‐, β‐ and γ‐cyclodextrins: Substitution at secondary hydroxyl groups and in vitro hydrolysis behavior

Journal of Pharmaceutical Sciences ◽

10.1002/1520-6017(200104)90:4<493::aid-jps1007>3.3.co;2-n ◽

2001 ◽

Vol 90 (4) ◽

pp. 493-503

Author(s):

Hideki Yano ◽

Fumitoshi Hirayama ◽

Hidetoshi Arima ◽

Kaneto Uekama

Keyword(s):

Hydroxyl Groups ◽

Secondary Hydroxyl ◽

In Vitro Hydrolysis

Halosugar nucleosides. II. Iodination of secondary hydroxyl groups of nucleosides with methyltriphenoxyphosphonium iodide

The Journal of Organic Chemistry ◽

10.1021/jo00834a002 ◽

1970 ◽

Vol 35 (9) ◽

pp. 2868-2877 ◽

Cited By ~ 47

Author(s):

Julien P. H. Verheyden ◽

John G. Moffatt

Keyword(s):

Hydroxyl Groups ◽

Secondary Hydroxyl

Regioselectivity among six secondary hydroxyl groups: selective acylation of the least reactive hydroxyl groups of inositol

Chemical Communications ◽

10.1039/c2cc17241k ◽

2012 ◽

Vol 48 (18) ◽

pp. 2448 ◽

Cited By ~ 15

Author(s):

Amol M. Vibhute ◽

Adiyala Vidyasagar ◽

Saritha Sarala ◽

Kana M. Sureshan

Keyword(s):

Hydroxyl Groups ◽

Secondary Hydroxyl ◽

Selective Acylation

Conversion of hydroxyl groups into bromo groups in carbohydrates with inversion of configuration

Canadian Journal of Chemistry ◽

10.1139/v81-053 ◽

1981 ◽

Vol 59 (2) ◽

pp. 339-343 ◽

Cited By ~ 53

Author(s):

Björn Classon ◽

Per J. Garegg ◽

Bertil Samuelsson

Keyword(s):

Elevated Temperature ◽

Hydroxyl Groups ◽

Secondary Hydroxyl ◽

Reaction Proceeds ◽

One Step ◽

High Yields

A novel reagent system is described for the efficient, one-step transformation of hydroxyl groups in carbohydrates to bromodeoxy groups. The reaction proceeds with inversion of configuration. The reagent system consists of triphenylphosphine, tribromoimidazole, and imidazole in toluene at elevated temperature. The carbohydrate need not be soluble in toluene. The examples given include substitution of isolated primary and secondary hydroxyl groups in otherwise protected carbohydrates as well as disubstitution involving one primary and one secondary position in hexopyranosides. High yields are obtained in the replacement of hydroxyl by bromine in the 2-position of 3,4,6-protected methyl α-D-gluco- and -mannopyranosides.

Regioselective monophosphorylation of glycols containing primary and secondary hydroxyl groups

Mendeleev Communications ◽

10.1070/mc2000v010n01abeh001212 ◽

2000 ◽

Vol 10 (1) ◽

pp. 3-4 ◽

Cited By ~ 2

Author(s):

Edward E. Nifantiev ◽

Mikhail K. Gratchev ◽

Stephen F. Martin

Keyword(s):

Hydroxyl Groups ◽

Secondary Hydroxyl

Inside Cover: Configurational Assignment of Secondary Hydroxyl Groups and Methyl Branches in Polyketide Natural Products through Bioinformatic Analysis of the Ketoreductase Domain (ChemBioChem 7/2013)

ChemBioChem ◽

10.1002/cbic.201390021 ◽

2013 ◽

Vol 14 (7) ◽

pp. 774-774

Author(s):

Andreas Kitsche ◽

Markus Kalesse

Keyword(s):

Natural Products ◽

Bioinformatic Analysis ◽

Hydroxyl Groups ◽

Secondary Hydroxyl ◽

Configurational Assignment

Trityl derivatives of cellobiose. IV. Studies on the relative reactivities of the secondary hydroxyl groups in 6,6'-di-O-tritylcellobiose and methyl 6,6'-di-O-trityl-.BETA.-cellobioside by selective acetylation.

Chemical and Pharmaceutical Bulletin ◽

10.1248/cpb.29.2776 ◽

1981 ◽

Vol 29 (10) ◽

pp. 2776-2784 ◽

Cited By ~ 5

Author(s):

KYOKO KOIZUMI ◽

TOSHIKO UTAMURA

Keyword(s):

Hydroxyl Groups ◽

Secondary Hydroxyl ◽

Derivatives Of

Preparation of prednisolone-appended α-, β- and γ-cyclodextrins: Substitution at secondary hydroxyl groups and in vitro hydrolysis behavior

Journal of Pharmaceutical Sciences ◽

10.1002/1520-6017(200104)90:4<493::aid-jps1007>3.0.co;2-w ◽

2001 ◽

Vol 90 (4) ◽

pp. 493-503 ◽

Cited By ~ 31

Author(s):

Hideki Yano ◽

Fumitoshi Hirayama ◽

Hidetoshi Arima ◽

Kaneto Uekama

Keyword(s):

Hydroxyl Groups ◽

Secondary Hydroxyl ◽

In Vitro Hydrolysis

Selective Benzoylation of Methyl 6-Deoxy-α- and β-D-glucopyranosides

Canadian Journal of Chemistry ◽

10.1139/v73-488 ◽

1973 ◽

Vol 51 (19) ◽

pp. 3272-3276 ◽

Cited By ~ 18

Author(s):

Yôtaro Kondo ◽

Kiyoshi Miyahara ◽

Naoki Kashimura

Keyword(s):

Major Product ◽

Hydroxyl Groups ◽

Secondary Hydroxyl

Selective dimolar benzoylation of methyl 6-deoxy-α- and β-D-glucopyranosides yielded the 2,3-di-O-benzoate of the respective glucopyranoside as the major product in 61 and 29% yields. The orders of the reactivity of the secondary hydroxyl groups in α- and β-anomers were different, i.e., the order was 2-OH > 3-OH > 4-OH for the former and 3-OH > 2-OH > 4-OH for the latter.

THE REACTIVITY OF CELLULOSE: III. THE NITRATION OF COTTON LINTERS ALTERNATELY WETTED WITH WATER AT VARIOUS TEMPERATURES AND DRIED, AND THE PROBABLE DISTRIBUTION OF THE NITRATE GROUPS

Canadian Journal of Chemistry ◽

10.1139/v59-058 ◽

1959 ◽

Vol 37 (2) ◽

pp. 444-453 ◽

Cited By ~ 5

Author(s):

T. P. Yin ◽

R. K. Brown

Keyword(s):

Lead Tetraacetate ◽

Hydroxyl Groups ◽

Secondary Hydroxyl ◽

Cotton Linters ◽

Probable Distribution

Cotton linters alternately wetted at 0° or 25° and dried show progressively greater ease of nitration paralleling the number of wetting–drying cycles. The reverse is found to be true for linters wetted at 50°, 75°, or 100°. Analysis of the data obtained from lead tetraacetate oxidation of the nitrates favors the depressive concept of nitration and indicates that the observed changes in reactivity occasioned by the wetting–drying treatments are largely due to greater alterations in the accessibility of the primary rather than the secondary hydroxyl groups.