21317-50-0Relevant academic research and scientific papers
Synthesis of the polyketomycin disaccharide
Micalizzi, Douglas S.,Dougherty, J. Patrick,Noecker, Lincoln A.,Smith, Garry R.,Giuliano, Robert M.
, p. 3183 - 3188 (2007/10/03)
The disaccharide portion of the anthracycline antibiotic polyketomycin consists of the trideoxy sugar D-amicetose attached to the methyl-branched sugar L-axenose. The polyketomycin disaccharide was synthesized from methyl 2,3,6-trideoxy-α-D-erythro-hexopyranoside (methyl α-D-amicetoside) and phenyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-1-thio-α,β-L-xylo- hexopyranoside. The key coupling step was carried out by N-bromosuccinimide activation of the thioglycoside and gave the desired α (1→4) linked disaccharide exclusively in 71% yield, which was debenzylated by sodium and liquid ammonia.
Thioanhydro sugars. Part IX: Enantiospecific synthesis of a polyhydroxythio lane, key intermediate for the preparation of glycosidase inhibitors bearing inner thiosulfonium salt
Izquierdo, Isidoro,Plaza, Maria T.,Asenjo, Rafael,Ramirez, Antonio
, p. 1417 - 1421 (2007/10/03)
(2R,3R,4S)-3,4-Dihydroxy-2-[(R)-1,2-dihydroxyethyl]thiolane (1,4-anhydro-4-thio-D-mannitol), 1 has been prepared from methyl 4,6-O-benzylidene-α-D-altropyranoside 2 in seven steps, the latter being readily available from commercial methyl α-D-glucopyranos
Polyketomycin, a new antibiotic from Streptomyces sp. MK277-AF1. II. Structure determination
Momose, Isao,Chen, Wei,Nakamura, Hikaru,Naganawa, Hiroshi,Iinuma, Hironobu,Takeuchi, Tomio
, p. 26 - 32 (2007/10/03)
A new antibiotic, polyketomycin, was isolated from the culture broth of Streptomyces sp. MK277-AF1. The structure was determined by various NMR spectroscopies, X-ray crystallographic analysis and degradation experiments.
Synthesis of the Methyl α-D-Glycosides of Amicetose, Perosamine and Janose
Kjoelberg, Ove,Neumann, Klaus
, p. 877 - 882 (2007/10/02)
New methods for the synthesis of tri- and di-deoxy sugar, namely methyl α-D-amicetoside, methyl α-D-perosaminoside and methyl α-D-janoside are described.The readily available methyl 6-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside has been used as chiral
Synthesis of some trideoxy-D-hexoses and derivatives thereof from D-glucono-1,5-lactone
Regeling,Chittenden
, p. 79 - 91 (2007/10/02)
Enantiospecific syntheses of methyl 2,3,4-trideoxy-α-D- and β-D-glycero-hexopyranoside (10 and 11), methyl α-D- and β-D-amicetopyranoside (24 and 25), (2S)-1,2-hexanediol (36), (2S)-1,2,6-hexanetriol (37), and some derivatives thereof from D-glucono-1,5-lactone are described. Enantiospecific syntheses of methyl 2,3,4-trideoxy-α-D- and -β-D-glycero-hexopyranoside (10 and 11), methyl α-D- and β-D-amicetopyranoside (24 and 25), (2S)-1,2-hexanediol (36), (2S)-1,2,6-hexanetriol (37), and some derivatives thereof from D-glucono-1,5-lactone are described.
Improved Synthesis of Secondary Hydroperoxides from Alcohols
Casteel, Dee Ann,Jung, Kyeong-Eun
, p. 2597 - 2598 (2007/10/02)
Secondary hydroperoxides have been prepared from secondary alcohols by conversion of the alcohol into its mesylate and subsequent reaction with anhydrous hydrazine followed by hydrogen peroxide and sodium peroxide.
SYNTHESIS OF METHYL 2,6-DIDEOXY-4-THIO-α-D-RIBO-HEXOPYRANOSIDE, A NEW THIO SUGAR FOUND IN CALICHEMICINS
Laak, Kai van,Scharf, Hans-Dieter
, p. 4505 - 4506 (2007/10/02)
The radically induced rearrangement of the 3,4-O-thionocarbonate 4 leads to the two regioisomeric thiolcarbonates 5 and 6, respectively.Alkaline hydrolysis affords the title compound 7 and its regioisomer 8.
NITRONE CYCLOADDITIONS WITH VINYL SILANES: THE TOTAL SYNTHESIS OF DEOXYSUGARS.
DeShong, Philip,Leginus, Joseph M.
, p. 5355 - 5358 (2007/10/02)
The total synthesis of (+/-)-rhodinose (2) and benzoxocin 4, a model system for the glycosidic moiety of nogalomycin, are reported.The key transformation in each reaction sequence involves the cycloaddition of a nitrone with vinyltrimethylsilane to produc
