An Improved Total Synthesis of Tubercidin

Huang, Haiyang; Ruan, Zhizhong; Hu, Tao; Xiao, Qiang

doi:10.6023/cjoc201402027

Cited by 2 publications

(2 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The 7-bromo substitute is critical for the above Vorbrüggen glycosylation, otherwise the reaction cannot proceed. The reason may be that the 7-bromo substituent can reduce the reactivity of N -9, which results in the deazapurine being more purine-like [ 20 , 26 , 27 , 28 , 29 ].…”

Section: Resultsmentioning

confidence: 99%

“…Our group has a long-standing interest in total synthesis and biological activity evaluation of naturally occurring 7-deazapurine nucleosides and their biological activities [ 18 , 19 , 20 , 21 , 22 ]. Because of the unique disaccharide structure and a great need for structure-based biological study, structural confirmation of 5′- O -α- d -glucopyranosyl tubercidin 2 and synthesis of its analogues in a concise and modular fashion are preferred.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

First Total Synthesis of 5′-O-α-d-Glucopyranosyl Tubercidin

Ouyang¹,

Huang²,

Yang³

et al. 2020

Marine Drugs

Self Cite

View full text Add to dashboard Cite

The first total synthesis of 5′-O-α-d-glucopyranosyl tubercidin was successfully developed. It is a structurally unique disaccharide 7-deazapurine nucleoside exhibiting fungicidal activity, and was isolated from blue-green algae. The total synthesis was accomplished in eight steps with 27% overall yield from commercially available 1-O-acetyl-2,3,5-tri-O-benzoyl-β-d-ribose. The key step involves stereoselective α-O-glycosylation of the corresponding 7-bromo-6-chloro-2′,3′-O-isopropylidene-β-d-tubercidin with 2,3,4,6-tetra-O-benzyl-glucopyranosyl trichloroacetimidate. All spectra are in accordance with the reported data for natural 5′-O-α-d-glucopyranosyl tubercidin. Meanwhile, 5′-O-β-d-glucopyranosyl tubercidin was also prepared using the same strategy.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

First Total Synthesis of 5′-O-α-d-Glucopyranosyl Tubercidin

Ouyang¹,

Huang²,

Yang³

et al. 2020

Marine Drugs

Self Cite

View full text Add to dashboard Cite

show abstract

Glycosylation of Pyrrolo[2,3-d]pyrimidines with 1-O-Acetyl-2,3,5-tri-O-benzoyl-β-d-ribofuranose: Substituents and Protecting Groups Effecting the Synthesis of 7-Deazapurine Ribonucleosides

2018

View full text Add to dashboard Cite

Glycosylation of nonfunctionalized 6-chloro-7-deazapurine with commercially available 1- O-acetyl-2,3,5-tri- O-benzoyl-β-d-ribofuranose (45%) followed by amination and deprotection gave tubercidin in only two steps. Similar conditions applied for the synthesis of 7-deazaguanosine employing pivaloylated 2-amino-6-chloro-7-deazapurine gave 18% glycosylation yield. The less bulky isobutyryl or acetyl protected amino group directed the glycosylation toward the exocyclic amino substituent. 7-Halogenated intermediates were glycosylated followed by dehalogenation to overcome the low glycosylation yield in the synthesis of 7-deazaguanosine.

show abstract

An Improved Total Synthesis of Tubercidin

Cited by 2 publications

References 8 publications

First Total Synthesis of 5′-O-α-d-Glucopyranosyl Tubercidin

First Total Synthesis of 5′-O-α-d-Glucopyranosyl Tubercidin

Glycosylation of Pyrrolo[2,3-d]pyrimidines with 1-O-Acetyl-2,3,5-tri-O-benzoyl-β-d-ribofuranose: Substituents and Protecting Groups Effecting the Synthesis of 7-Deazapurine Ribonucleosides

Contact Info

Product

Resources

About