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Convenient Synthesis Of 1,4-Dideoxy-1,4-imino-D-ribitol From D-Ribose

M. Oba, S. Kawaji, Hironobu Kushima, Takanori Sano, Kozaburo Nishiyama
Published 2013 · Chemistry

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This paper describes a convenient synthesis of 1,4-dideoxy-1,4-imino-D-ribitol (DRB) from D-ribose. L-Lyxonolactone, a key intermediate in this synthesis, was prepared by base-promoted hydrolysis of a 5-chlorinated D-ribonolactone derivative with inversion of configuration at the C-4 position. Cyclization of the generated dimesylated L-lyxitol with benzylamine proceeded with another configurational inversion at C-4 to afford the D-ribo-configured pyrrolidine system, which upon deprotection gave DRB.
This paper references
C
E. C. Bigham (1984)
G
K. Clinch (2006)
10.3891/ACTA.CHEM.SCAND.48-0675
Synthesis of L-Ribono- and L-Lyxono-lactone.
Henriette Kold (1994)
and S
V.L.A. Malladi (2011)
10.1021/JM00372A003
Inhibition of arabinose 5-phosphate isomerase. An approach to the inhibition of bacterial lipopolysaccharide biosynthesis.
E. Bigham (1984)
10.1021/JA00210A026
Chemistry of F1,F0-ATPase inhibitors. Stereoselective total syntheses of (+)-citreoviral and (-)-citreoviridin
H. Suh (1988)
10.1016/j.carres.2008.02.014
Stereoselective synthesis of 4'-selenonucleosides using the Pummerer glycosylation reaction.
K. Jayakanthan (2008)
and K
N. Asano (1994)
10.1002/CHIN.198836205
Polyhydroxylated Pyrrolidines from Sugar Lactones: Synthesis of 1,4-Dideoxy-1,4-imino-D-glucitol from D-Galactonolactone and Syntheses of 1,4-Dideoxy-1,4-imino-D-allitol, 1,4-Dideoxy-1,4-imino-D-ribitol, and (2S,3R,4S)-3,4-Dihydroxypr
G. W. J. Fleet (1988)
10.1046/J.1432-1327.2001.01837.X
Novel alpha-L-fucosidase inhibitors from the bark of Angylocalyx pynaertii (Leguminosae).
N. Asano (2001)
10.1016/J.TETASY.2006.12.023
Enantioselective synthesis of hydroxylated pyrrolidines via Sharpless epoxidation and olefin metathesis
C. Murruzzu (2007)
10.1016/S0006-291X(03)00540-0
The inhibitory action of pyrrolidine alkaloid, 1,4-dideoxy-1,4-imino-D-ribitol, on eukaryotic DNA polymerases.
Y. Mizushina (2003)
10.1515/9783486731620-002
I
John B. Shoven (1824)
10.1016/S0957-4166(02)00033-2
Asymmetric synthesis of 1,4-dideoxy-1,4-imino-d-ribitol via stereoselective addition of allylphenylsulfone to an aryl N-sulfinylimine
R. Kumareswaran (2002)
and C
H. Kold (1994)
10.1016/j.bmc.2011.07.043
Inhibition of LuxS by S-ribosylhomocysteine analogues containing a [4-aza]ribose ring.
Venkata L A Malladi (2011)
N
Y. Mizushina (2003)
andM
H. Setoi (1987)
10.1016/j.bmc.2008.05.056
N-Arylmethyl substituted iminoribitol derivatives as inhibitors of a purine specific nucleoside hydrolase.
A. Goeminne (2008)
10.1016/J.TETLET.2006.02.092
Asymmetric synthesis of α-amino aldehydes from sulfinimine (N-sulfinyl imine)-derived α-amino 1,3-dithianes. Formal synthesis of (−)-2,3-trans-3,4-cis-dihydroxyproline
F. A. Davis (2006)
10.1016/S0040-4020(01)81717-8
Synthesis from d-mannose of 1,4-dideoxy-1,4-imino-l-ribitol and of the α-mannosidase inhibitor 1,4-dideoxy-1,4-imino-d-talitol
G. Fleet (1988)
10.1016/S0040-4039(00)79290-2
A new class of C-nucleoside analogues. 1-(S)-aryl-1,4-dideoxy-1,4-imino-D-ribitols, transition state analogue inhibitors of nucleoside hydrolase
B. Horenstein (1993)
10.1017/CBO9781139207249.009
I and J
William M. Marsden (2012)
10.1002/CHIN.199418230
A New Class of C‐Nucleoside Analogues. 1‐(S)‐Aryl‐1,4‐dideoxy‐1,4‐ imino‐D‐ribitols, Transition State Analogue Inhibitors of Nucleoside Hydrolase.
B. Horenstein (1994)
10.1021/NP010360F
New sugar-mimic alkaloids from the pods of Angylocalyx pynaertii.
K. Yasuda (2002)
and L
J. D. Williams (2005)
10.1248/CPB.35.3995
Synthesis of some polyhydroxylated pyrrolidine derivatives.
H. Setoi (1987)
10.1002/CHIN.200305069
O‐(1‐Phenylbutyl)benzyloxyacetaldoxime, a Versatile Reagent for the Asymmetric Synthesis of Protected 1,2‐Amino Alcohols and 2‐Hydroxymethyl Nitrogen Heterocycles.
Tracey S. Cooper (2003)
T
K. Yasuda (2002)
10.1177/146642407409400210
(b)
Miss A.O. Penney (1974)
10.1016/0008-6215(94)84059-8
Synthesis of (2R,3R,4S)-2-hydroxymethylpyrrolidine-3,4-diol from (2S)-3,4-dehydroproline derivatives.
D. M. Goli (1994)
10.1016/J.TETASY.2009.10.004
Looking glass inhibitors: both enantiomeric N-benzyl derivatives of 1,4-dideoxy-1,4-imino-d-lyxitol [a potent competitive inhibitor of α-d-galactosidase] and of 1,4-dideoxy-1,4-imino-l-lyxitol [a weak competitive inhibitor of α-d-galactosidase] inhibit naringinase, an α-l-rhamnosidase competitively
Thomas B. Mercer (2009)
O-(1-phenylbutyl)benzyloxyacetaldoxime
T. S. Cooper (2002)
10.1055/S-2002-34235
O-(1-Phenylbutyl)benzyloxyacetaldoxime, a Versatile Reagent for the Asymmetric Synthesis of Protected 1,2-Aminoalcohols and 2-Hydroxymethyl Nitrogen Heterocycles
Tracey S. Cooper (2002)
10.1002/0471264229.OS082.12
D‐Ribonolactone and 2,3‐Isopropylidene(D‐Ribonolactone)
J. Williams (2005)
10.1016/S0040-4020(01)81716-6
Polyhydroxylated pyrrolidines from sugar lactomes: Synthesis of 1,4-dideoxy-1,4-imino-d-glucitol from d-galactonolactone and syntheses of 1,4-dideoxy-1,4-imino-d-allitol, 1,4-dideoxy-1,4-imino-d-ribitol, and (2s,3r,4s)-3,4-dihydroxyproline from d-gulonolactone
G. Fleet (1988)
10.1002/CHIN.197701106
RULES FOR RING CLOSURE
J. Baldwin (1977)
and E
F. A. Davis (2006)
10.1021/OP050222N
A Concise, Efficient and Production-Scale Synthesis of a Protected l-Lyxonolactone Derivative: An Important Aldonolactone Core
H. Batra (2006)
10.1039/B517883E
Syntheses and bio-activities of the L-enantiomers of two potent transition state analogue inhibitors of purine nucleoside phosphorylases.
K. Clinch (2006)
10.1016/S0263-8762(97)71569-7
Organic Process Research and Development
A. Hall (1997)
10.1016/0008-6215(94)84060-1
N-containing sugars from Morus alba and their glycosidase inhibitory activities.
N. Asano (1994)
10.1016/J.EJMECH.2007.03.027
Synthesis and biochemical evaluation of guanidino-alkyl-ribitol derivatives as nucleoside hydrolase inhibitors.
A. Goeminne (2008)
G
A. Goeminne (2008)
H
N. Asano (2001)



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