A chiral approach to 2-deoxystreptamine

1987 ◽  
Vol 65 (7) ◽  
pp. 1443-1451 ◽  
Author(s):  
Hans H. Baer ◽  
Isamu Arai ◽  
Bruno Radatus ◽  
June Rodwell ◽  
Nguyen Chinh
Keyword(s):  
Catalytic Hydrogenation ◽  
Periodate Oxidation ◽  
Optically Active ◽  
Potential Utility ◽  
Isopropylidene Derivative ◽  
Chiral Intermediates ◽  
New Synthesis ◽  
Compound 21 ◽  
Derivatives Of

A new synthesis of 2-deoxystreptamine (21), a component of numerous antibiotics, was developed. Starting from D-mannose, it proceeds through chiral intermediates and is designed to furnish starting points for the preparation of stereospecifically modified derivatives of the meso compound 21. 1,2-Dideoxy-1-nitro-D-manno-heptitol (2), obtainable from mannose by the nitromethane method, was protected as the 4,5:6,7-di-O-isopropylidene derivative 4, which was mesylated or triflated in position 3. From the sulfonic esters (5 and 6) two different routes involving displacement by azide, partial deacetonation at O-6,7, periodate oxidation, and cyclization of the resulting nitroaldohexose derivatives converged to give 1L-(1,3/2,4,6)-6-azido-1,2-O-isopropylidene-4-nitro-1,2,3-cyclohexanetriol (19) as a key intermediate. Catalytic hydrogenation then afforded optically active 4,5-O-isopropylidene-2-deoxystreptamine (23), isolated as its N,N′-diacetyl derivative 24. Deacetonation of 19 gave the azidonitrotriol 15, which was reduced to 21. The potential utility of the chiral intermediates for stereospecific syntheses of deoxystreptamine-containing aminoglycosides is discussed.

Novel optically active organometallic derivatives of fullerenes with non-central types of chirality in addends: synthetic and CD studies

2009 ◽  
Vol 50 (38) ◽  
pp. 5347-5350 ◽  
Author(s):  
Viatcheslav I. Sokolov ◽  
Vasily V. Bashilov ◽  
Fedor M. Dolgushin ◽  
Natalya V. Abramova ◽  
Kyrill K. Babievsky ◽  
...  
Keyword(s):  
Optically Active ◽  
Cd Studies ◽  
Derivatives Of

scholarly journals Synthesis of 2-aminosuberic acid derivatives as components of some histone deacetylase inhibiting cyclic tetrapeptides

2017 ◽  
Vol 13 ◽  
pp. 2153-2156 ◽  
Author(s):  
Shital Kumar Chattopadhyay ◽  
Suman Sil ◽  
Jyoti Prasad Mukherjee
Keyword(s):  
Amino Acid ◽  
Histone Deacetylase ◽  
Building Block ◽  
Suberic Acid ◽  
Metathesis Reaction ◽  
Cross Metathesis ◽  
Important Amino Acid ◽  
New Synthesis ◽  
Cyclic Tetrapeptides ◽  
Derivatives Of

A new synthesis of the important amino acid 2-aminosuberic acid from aspartic acid is reported. The methodology involves the alternate preparation of (S)-2-aminohept-6-enoate ester as a building block and its diversification through a cross-metathesis reaction to prepare the title compounds. The utility of the protocol is demonstrated through the preparation of three suberic acid derivatives of relevance to the design and the synthesis of peptides of biological relevance.

Selective catalytic hydrogenation of unsaturated derivatives of nitrobenzene in alcoholic media

1999 ◽  
Vol 144 (1) ◽  
pp. 199-206 ◽  
Author(s):  
E. Lamy-Pitara ◽  
B. N'Zemba ◽  
J. Barbier ◽  
F. Barbot ◽  
L. Miginiac
Keyword(s):  
Catalytic Hydrogenation ◽  
Derivatives Of

ChemInform Abstract: REACTIVITY OF ORGANOTIN COMPOUNDS. XII. SYNTHESIS OF OPTICALLY ACTIVE INDENYL L DERIVATIVES OF TIN

1978 ◽  
Vol 9 (27) ◽  
Author(s):  
A. N. KASHIN ◽  
V. A. KHUTORYANSKII ◽  
V. N. BAKUNIN ◽  
I. P. BELETSKAYA ◽  
O. A. REUTOV
Keyword(s):  
Optically Active ◽  
Organotin Compounds ◽  
Derivatives Of

Asymmetric synthesis. Production of optically active amino acids by catalytic hydrogenation

1977 ◽  
Vol 99 (19) ◽  
pp. 6262-6267 ◽  
Author(s):  
M. D. Fryzuk ◽  
B. Bosnich
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Catalytic Hydrogenation ◽  
Optically Active

scholarly journals Covalent labelling of ligand binding sites of human placental S-adenosylhomocysteine hydrolase with 8-azido derivatives of adenosine and cyclic AMP

1985 ◽  
Vol 232 (3) ◽  
pp. 643-650 ◽  
Author(s):  
V N Aiyar ◽  
M S Hershfield
Keyword(s):  
Cyclic Amp ◽  
Binding Sites ◽  
Catalytic Mechanism ◽  
Periodate Oxidation ◽  
Regulatory Subunit ◽  
Adenosylhomocysteine Hydrolase ◽  
Dependent Protein ◽  
Covalently Linked ◽  
The Relationship ◽  
Derivatives Of

S-Adenosylhomocysteine hydrolase (AdoHcyase) has previously been identified as a cytoplasmic adenosine and cyclic AMP binding protein. In order to examine the relationship between the adenosine and cyclic AMP binding sites on this enzyme we have explored the use of 8-azido analogues of adenosine and cyclic AMP as photoaffinity reagents for covalently labelling AdoHcyase purified from human placenta. 8-Azidoadenosine (8-N3-Ado), like adenosine, inactivated AdoHcyase, and the rate of inactivation was greatly increased by periodate oxidation. In addition, 8-N3-Ado was found to participate in the first step in the catalytic mechanism for AdoHcyase, resulting in conversion of enzyme-bound NAD+ to NADH, although it was not a substrate for the full enzyme-catalysed reaction. Radioactively labelled 8-N3-Ado, its periodate-oxidized derivative and 8-azidoadenosine 3′, 5′-phosphate (8-N3-cAMP) bound specifically to adenosine binding sites on AdoHcyase and, after irradiation, became covalently linked to the enzyme. Photoaffinity-labelled enzyme could be precipitated by monoclonal antibody to human AdoHcyase. Two observations suggested that cyclic AMP and adenosine bind to the same sites on AdoHcyase. First cyclic AMP and adenosine each blocked binding of both radioactively labelled 8-N3-Ado and 8-N3-cAMP, and second, digestion with V8 proteinase generated identical patterns of peptides from AdoHcyase that had been photolabelled with [32P]8-N3-cAMP and [3H]8-N3-Ado. Binding sites for cyclic AMP on AdoHcyase were found to differ functionally and structurally from cyclic AMP binding sites on the R1 regulatory subunit of cyclic AMP-dependent protein kinase.

New Synthesis of Derivatives of 6-Aryl-3-methyl-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b] [1,3,4]thiadiazine-7-carboxylic Acid.

ChemInform ◽  
2004 ◽  
Vol 35 (8) ◽  
Author(s):  
V. A. Yanchenko ◽  
V. V. Malyshev ◽  
A. M. Demchenko ◽  
M. O. Lozinskii
Keyword(s):  
Carboxylic Acid ◽  
New Synthesis ◽  
Derivatives Of

Synthesis of 5'-O-phosphonomethyl derivatives of pyrimidine 2'-deoxynucleosides

1990 ◽  
Vol 55 (10) ◽  
pp. 2521-2536 ◽  
Author(s):  
Marcela Krečmerová ◽  
Hubert Hřebabecký ◽  
Antonín Holý
Keyword(s):  
Sodium Salt ◽  
Catalytic Hydrogenation ◽  
Bond Cleavage ◽  
Diethyl Ester ◽  
Derivatives Of

Reaction of sodium salt of 3-N,3'-O-bis(benzyloxymethyl)-2'-deoxyuridine (X) and 3-N,3'-O-bis(benzyloxymethyl)-2'-deoxythymidine (XI) with diethyl p-toluenesulfonyloxymethanephosphonate in dimethylformamide afforded diesters of the respective 5'-O-phosphonomethyl derivatives XII and XVII. Diethyl esters of 5'-O-phosphonomethyl-2'-deoxynucleosides XV and XIX, obtained after hydrogenolytic removal of the benzyloxymethyl groups, were converted into free 2'-deoxy-5'-O-phosphonomethyluridine (XVI) and a mixture of anomeric 1-(2-deoxy-5-O-phosphonomethyl-β-D-erythro-pentofuranosyl)thymines (XXIIIa, XXIIIb), respectively. Analogously, 2'-deoxy-5'-O-phosphonomethylcytidine (XXXIV) was prepared from 4-N-benzoyl-2'-deoxy-3'-O-(tetrahydro-2H-pyran-2-yl) cytidine (XXX) via diethyl ester of 2'-deoxy-5'-O-phosphonomethylcytidine (XXXIII). This compound reacted with bromotrimethylsilane to give compound XXXIV without anomerization and nucleoside bond cleavage. Condensation of the protected nucleosides X and XI with dibenzyl p-toluenesulfonyloxymethanephosphonate afforded dibenzyl esters of the corresponding 5'-O-phosphonomethyl derivatives XIII and XVIII. The free 5'-O-phosphonomethyl derivatives XVI and XXIIIa were obtained from XIII and XVIII by catalytic hydrogenation.

ChemInform Abstract: STEREOCHEMICAL STUDIES OF ADRENERGIC DRUGS. OPTICALLY ACTIVE DERIVATIVES OF IMIDAZOLINES

1977 ◽  
Vol 8 (16) ◽  
pp. no-no
Author(s):  
D. D. MILLER ◽  
F. L. HSU ◽  
R. R. JUN. RUFFOLO ◽  
P. N. PATIL
Keyword(s):  
Optically Active ◽  
Adrenergic Drugs ◽  
Derivatives Of
Sign in / Sign up

Export Citation Format

Share Document