An Efficient Synthetic Route for a Versatile Ciliapterin Derivative and the First Ciliapterin D-Mannoside Synthesis

Hanaya, Tadashi; Baba, Hiroki; Kanemoto, Masashi; Yamamoto, Hiroshi

doi:10.3987/com-08-s(n)54

Cited by 10 publications

(5 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For the diastereoselective formation of 5 bearing a tetrasubstituted asymmetric center at the C4′ position, we envisaged the use of the aldol reaction of protected 3-keto furanose 6 with formaldehyde. Based on a literature precedent, treatment of 6 under suitable basic conditions was anticipated to produce an enolate intermediate with a double bond at the C3′–C4′ position. The electrophilic approach of formaldehyde to the enolate from the less hindered β-face would then give 5 in a diastereoselective manner.…”

mentioning

confidence: 99%

Synthesis of EFdA via a Diastereoselective Aldol Reaction of a Protected 3-Keto Furanose

2015

View full text Add to dashboard Cite

An efficient enantioselective total synthesis of EFdA, a remarkably potent anti-HIV nucleoside analogue with various favorable pharmacological profiles, has been achieved in 37% overall yield from diacetone-D-glucose by a 14-step sequence that features a highly diastereoselective installation of the tetrasubstituted stereogenic center at the C4' position, direct oxidative cleavage of an acetonide-protected diol derivative to an aldehyde, and one-pot 2'-deoxygenation of a ribonucleoside intermediate.

show abstract

mentioning

confidence: 99%

Synthesis of EFdA via a Diastereoselective Aldol Reaction of a Protected 3-Keto Furanose

2015

View full text Add to dashboard Cite

show abstract

“…Glycosides of L-threo-biopterin and 6-hydroxymethylpterin were also isolated from green sulfur bacteria and cyanobacteria (8)(9)(10). Some of these structures have been confirmed also by chemical syntheses (11)(12)(13)(14)(15)(16).…”

Section: Introductionmentioning

confidence: 85%

An Efficient Synthesis of 2'-O-(β-D-Ribofuranosyl)biopterin

et al. 2008

Self Cite

View full text Add to dashboard Cite

N2-(N,N-Dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]-1',2'-di-O-(trimethylsilyl)biopterin (4) was prepared from biopterin (1a, 86% overall yield) in 5 steps. Glycosylation of 4 with 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose (5a) and its 2,3,5-tri-O-benzoyl analog (5b) respectively afforded the corresponding 2'-O-(2,3,5-tri-Oacetyl- and 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)biopterin derivatives (6a, 42% and 6b, 60%) as major products. Removal of the protecting groups of 6b provided 2'-O-(β-D-ribofuranosyl)biopterin (1c, 87% overall yield) in 3 steps.

show abstract

“…Successive removal of the protecting groups of 28 (using the same procedures described for 1d from 20 in Scheme ) has enabled the first synthesis of tepidopterin ( 2e ) (36). Similarly, 2′‐ O ‐(α‐ D ‐mannopyranosyl)ciliapterin ( 2c ) has been prepared from the 1′‐ O ‐PMB‐ciliapterin derivative ( 21 ) (39).…”

Section: Synthesis Of Tepidopterin (2e)mentioning

confidence: 99%

Synthesis of biopterin and related pterin glycosides

Hanaya

Yamamoto

2013

IUBMB Life

Self Cite

View full text Add to dashboard Cite

Certain pterins having a hydroxyalkyl side chain at C-6 have been found as glycosidic forms in certain prokaryotes, such as 2'-O-(α-D-glucopyranosyl)biopterin from various kinds of cyanobacteria, and limipterin from a green sulfur photosynthetic bacterium. Synthetic studies on glycosides of biopterin and related pterins have been made in view of the structural proof as well as for closer examination of their biological activities and functions. The syntheses of these natural pterin glycosides have effectively been achieved, mostly through appropriately protected N(2) -(N,N-dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]pterin derivatives as glycosyl acceptors, and are reviewed here.

show abstract

An Efficient Synthetic Route for a Versatile Ciliapterin Derivative and the First Ciliapterin D-Mannoside Synthesis

Cited by 10 publications

References 27 publications

Synthesis of EFdA via a Diastereoselective Aldol Reaction of a Protected 3-Keto Furanose

Synthesis of EFdA via a Diastereoselective Aldol Reaction of a Protected 3-Keto Furanose

An Efficient Synthesis of 2'-O-(β-D-Ribofuranosyl)biopterin

Synthesis of biopterin and related pterin glycosides

Contact Info

Product

Resources

About