Synthesis, crystal structure, and conformation of methyl 6-deoxy-2,3-O-isopropylidene-α-d-manno-heptofuranoside

Krajewski, J. W.; Gluziński, P.; Pakulski, Zbigniew; Zamojski, Aleksander; Mishnev, A. F.; Ķemme, A.

doi:10.1016/0008-6215(94)90008-6

Cited by 13 publications

(5 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Decomplexation, separation from the -L-gulo diastereomer 44 and reduction of the 6-deoxyhepturonate 43 afforded the methyl 2,3-O-isopropylidene--D-manno-heptofuranoside 45 in 20% yield, which was eventually converted into 6-deoxy-D-mannoheptose 3 " Fig. (10)" [101,102].…”

Section: Oacmentioning

confidence: 99%

Occurrence, Synthesis and Biosynthesis of Bacterial Heptoses

Kosma

2008

COC

View full text Add to dashboard Cite

Heptoses are important higher-carbon sugars occurring in numerous structural variations in several domains of the bacterial cell wall, which are briefly summarized. Recent approaches towards the chemical and chemo-enzymatic synthesis of these microbial monosaccharides will be summarized as well as progress made in the elucidation of two major biochemical pathways involving the synthesis of heptose phosphates and nucleotide-activated heptoses.

show abstract

Section: Oacmentioning

confidence: 99%

Occurrence, Synthesis and Biosynthesis of Bacterial Heptoses

Kosma

2008

COC

View full text Add to dashboard Cite

show abstract

“…In this case also, only one regioisomer is obtained, whose Reactions with the First and Third Generations of the structure could be deduced from 13 C-NMR spectra. Indeed, Dendrimer all CH 2 groups are nonequivalent for compound 7ЈЈ; they would give 11 signals (labeled aϪk), whereas 6 signals are As seen above, the reaction of the model compound with tetraazamacrocycles leads cleanly to the formation of only expected for both compounds 7 and 7Ј.…”

Section: Resultsmentioning

confidence: 98%

Grafting of Tetraazamacrocycles on the Surface of Phosphorus-Containing Dendrimers

et al. 1999

View full text Add to dashboard Cite

Three types of tetraazamacrocycles (1,4,8,11‐tetraazacyclotetradecane, 1,4,8,12‐tetraazacyclopentadecane, and 1,4,8,11‐tetraazacyclotetradecane‐5,7‐dione) are grafted on the surface of phosphorus‐containing dendrimers possessing P(S)Cl2 end groups (for generations 1 and 3: this corresponds to three and twelve macrocycles, respectively) and on the model compound PhCHNN(Me)P(S)Cl2. Depending on the nature of the macrocycle, the reaction induces the formation of five‐membered rings (diazaphospholanes) or of six‐membered rings (diazaphosphorinanes). The structure of the adducts is deduced from 13C NMR spectra and from X‐ray diffraction studies of the reaction products (8, 9, 10) of the model compound.

show abstract

“…Application of the Kiliani cyanohydrin synthesis to methyl 6-deoxy-2,3- O -isopropylidene-α- d - lyxo -hexofuranosid-5-ulose ( 1 ) [6] (prepared from methyl 2,3- O -isopropylidene-α- d - lyxo -pentodialdo-1,4-furanoside [7,8] by the Grignard reaction with methylmagnesium iodide and subsequent oxidation of the reaction product with pyridinium dichromate) led to the formation of methyl 5-cyano-6-deoxy-2,3- O -isopropylidene-β- l -gulofuranoside ( 2 ) (Scheme 1). The almost 92% isolated yield of 2 indicates a high stereoselectivity for the cyanohydrin formation.…”

Section: Resultsmentioning

confidence: 99%