A NEW SYNTHESIS OF METHYL β-D-GULOPYRANOSIDE

1960 ◽  
Vol 38 (10) ◽  
pp. 1917-1920 ◽  
Author(s):  
N. J. Antia ◽  
M. B. Perry
Keyword(s):  
Carbon Atom ◽  
Sodium Borohydride ◽  
Convenient Method ◽  
Reaction Scheme ◽  
Synthetic Route ◽  
Sodium Metaperiodate ◽  
New Synthesis

The oxidation of 1 mole of β-D-glycero-D-gulo-heptopyranoside with 1 mole of sodium metaperiodate, followed by reduction with sodium borohydride, gave rise to crystalline methyl β-D-gulopyranoside. The method provides a new synthetic route to the D-guloside and, thence, to D-gulose. The possibility of utilizing this reaction scheme as a general convenient method for preparing the relatively rare aldohexoses as well as for "labelling" carbon atom 1 of these compounds is discussed.

Flavan derivatives. XXIII. Preparation and synthetic applications of Flav-3-enes

1968 ◽  
Vol 21 (9) ◽  
pp. 2247 ◽  
Author(s):  
JW Clark-Lewis ◽  
RW Jemison
Keyword(s):  
Sodium Borohydride ◽  
Acidic Medium ◽  
Catalytic Reduction ◽  
Heterocyclic Ring ◽  
High Yield ◽  
Lithium Aluminium Hydride ◽  
Lower Field ◽  
Field Characteristic ◽  
Lithium Aluminium ◽  
New Synthesis

2'-Hydroxychalcones and α-alkoxy-2'-hydroxychalcones are converted by sodium borohydride in isopropanol into flav-3-enes and 3-alkoxyflav-3-enes in the convenient new synthesis which makes these flavenes readily available. Catalytic reduction of the flavenes gives the corresponding flavans or 3-alkoxyflavans in high yield, and the latter are obtained mainly in the 2,s-cis-form. The flavenes immediately give flavs lium cations in the cold when treated with acids in air, and oxidation of 5,7,3',4'-tetramethoxyflav-3-ene with benzoquinone in an acidic medium gave the flavylium salt, isolated as the ferrichloride. Reduction of 5,7,3',4'-tetramethoxy-flavylium chloride with lithium aluminium hydride gave 5,7,3',4'-tetramethoxy-flav-2-ene identical with the flavene obtained from (-)-epicatechin tetramethyl ether, and confirms an earlier investigation by Gramshaw, Johnson, and King. In its N.M.R. spectrum the heterocyclic-ring protons of this flav-2-ene give an ABX multiplet which is easily distinguished from the ABX multiplet at much lower field characteristic of flav-3-enes.

Anisotropic manganese antimonide nanoparticle formation by solution–solid–solid growth mechanism: consequence of sodium borohydride addition towards reduced surface oxidation and enhanced magnetic moment

Nanoscale ◽  
2019 ◽  
Vol 11 (14) ◽  
pp. 6886-6896 ◽  
Author(s):  
Malsha A. Hettiarachchi ◽  
Ehab Abdelhamid ◽  
Boris Nadgorny ◽  
Stephanie L. Brock
Keyword(s):  
Growth Mechanism ◽  
Sodium Borohydride ◽  
Magnetic Moment ◽  
Surface Oxidation ◽  
Solution Phase ◽  
Synthetic Route ◽  
Nanoparticle Formation ◽  
Reduced Surface

Novel synthetic route to synthesize solution-phase anisotropic MnSb nanoparticles was developed and the solution–solid–solid growth mechanism was elucidated.

ChemInform Abstract: Convenient Method for Reduction of C-N Double Bonds in Oximes, Imines, and Hydrazones Using Sodium Borohydride-Raney Ni System.

ChemInform ◽  
2012 ◽  
Vol 43 (46) ◽  
pp. no-no
Author(s):  
Yihua Yang ◽  
Shouxin Liu ◽  
Junzhang Li ◽  
Xia Tian ◽  
Xiaoli Zhen ◽  
...  
Keyword(s):  
Sodium Borohydride ◽  
Convenient Method ◽  
Double Bonds ◽  
Raney Ni

Chemistry of the Podocarpaceae. XLVIII. Photo-sensitized oxidations of unsaturated ring-c aromatic diterpenoids

1974 ◽  
Vol 27 (9) ◽  
pp. 2001 ◽  
Author(s):  
RC Cambie ◽  
RC Hayward
Keyword(s):  
Sodium Borohydride ◽  
Convenient Method ◽  
Lithium Aluminium ◽  
Enol Acetates ◽  
High Yields ◽  
General Method

Photo-sensitized oxidation of the 6,7-dehydro ring-c aromatic diterpenoids (5), (8) and (38) affords high yields of the corresponding 5-ene-7-ones (62), (63) and (69). Similar oxygenation of 13-methoxy- totara-6,8,11,13-triene (21) gives a hydroperoxide (74) which undergoes a facile rearrangement to a naphthyl derivative (80) in the presence of acid. Photo-sensitized oxidation of the enol acetates derived from the 7-oxo diterpenoids, however, provides a general method for preparation of the corresponding 5-ene-7-one. Reduction of the enone (62) with lithium aluminium hydridealuminium chloride gives a mixture of the 5,8,11,13-tetraene (66) and the 6,8,11,13-tetraene (9) while reduction with sodium borohydride and treatment of the resulting alcohols (61) and (67) with acid gives a mixture of the tetraenes (5) and (68). Photo-oxygenation of the latter mixture provides a convenient method for isolating the tetraene (68). Similar reductions of 13-methoxytotara-5,8,11,13-tetraen-7-one (76) have been examined and products from the action of m-chloroperbenzoic acid on the enol acetates (19), (20) and (7) are reported.

Aril Azines. II. Hydrogenation of p-Tolil Monoazine

1975 ◽  
Vol 53 (5) ◽  
pp. 748-752 ◽  
Author(s):  
Peter Yates ◽  
E. M. Levi
Keyword(s):  
Hydrogen Atom ◽  
Carbon Atom ◽  
Sodium Borohydride ◽  
Sodium Methoxide ◽  
Major Product ◽  
Lead Tetraacetate ◽  
Ring Closure ◽  
Carbonyl Carbon Atom ◽  
Carbonyl Carbon ◽  
Independent Synthesis

Hydrogenation of p-tolil monoazine (1b) over palladium-on-charcoal gives as the major product 4,5-dihydro-5-(p-toluyl)-3,4,5-tri-(p-tolyl)-1H-pyrazol-4-ol (2b), which has previously been obtained by treatment of 1b with sodium methoxide. Several minor products are formed, which include p-tolualdehyde, p-toluic acid, and p-toluamide, p-tolunitrile, p-tolualazine, and 3,4,5-tri-(p-tolyl)-4H-pyrazo-4-ol (9). The structure of the last compound, which is also formed on reduction of 1b with sodium borohydride, was established by its independent synthesis from 1,2,3-tri-(p-tolyl)-1,3-propanedione by oxidation with lead tetraacetate followed by treatment with hydrazine. It is suggested that 2b arises via reduction of a C=N bond of 1b and aldol ring closure. The minor hydrogenation products are of interest in that their formation involves C—C hydrogenolysis; it is suggested that this is initiated by addition of a hydrogen atom to a carbonyl carbon atom of 1b.

scholarly journals Aberrant sialylation of granulocyte membranes in chronic myelogenous leukemia

Blood ◽  
1984 ◽  
Vol 63 (5) ◽  
pp. 1194-1197 ◽  
Author(s):  
MA Baker ◽  
RN Taub ◽  
CH Whelton ◽  
A Hindenburg
Keyword(s):  
Sialic Acid ◽  
Membrane Protein ◽  
Chronic Myelogenous Leukemia ◽  
Sodium Borohydride ◽  
Peripheral Blood ◽  
Gel Electrophoresis ◽  
Myelogenous Leukemia ◽  
Galactose Oxidase ◽  
Sodium Metaperiodate ◽  
Clinical Drug

Abstract Peripheral blood granulocytes from patients with chronic myelogenous leukemia (CML) were studied for accessibility of membrane sialic acid and galactose residues to sodium borohydride-3H radiolabeling after oxidation with sodium metaperiodate (PI/B3H4) or with galactose oxidase (GO/B3H4). Granulocytes from untreated patients with chronic myelogenous leukemia showed increased radiolabeling with PI/B3H4, and decreased labeling with GO/B3H4 when compared to normal granulocytes. Granulocytes from leukemic patients receiving chemotherapy showed normal labeling patterns. Gel electrophoresis of membrane extracts showed that the changes in PI/B3H4 and GO/B3H4 reactivity of CML cells were distributed over all membrane protein bands. Our data suggest that CML granulocyte membrane proteins are aberrantly sialylated, with decreased accessibility of galactose residues, and that these changes may be reversed by clinical drug treatment.

Sign in / Sign up

Export Citation Format

Share Document