328386-16-9

Upstream product

• 212776-53-9 4-(tert-Butyl-diphenyl-silanyloxymethyl)-5H-furan-2-one 
• 36679-81-9 4-hydroxymethyl-1,2,3,4-tetrahydrofuran-2-one 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 80904-75-2 4-hydroxymethyl-5H-furan-2-one 

Downstream Products

• 530098-83-0 4-(tert-butyl-diphenyl-silanyloxy)-3-hydroxymethyl-N,N-dimethyl-butyramide 

Relevant academic research and scientific papers

A new synthetic entry to furofuranoid lignans, methyl piperitol and fargesin

An efficient and general process is described for the preparation ofthe unsymmetrically substituted diequatorial and axial-equatorial furofuran lignans, methyl piperitol and fargesin. The synthetic strategy is based on a stereoselective manner by nucleoph

Structure-activity relationships of apio nucleosides as potential antiviral agents

Several types of novel apio nucleosides were synthesized starting from 1,3-dihydroxyacetone and evaluated for antiviral activity. Among compounds tested, amino substituted apio dideoxynucleosides exhibited anti-HBV activity, while thioapio dideoxynucleosides were found to be active against HIV-1. Apio dideoxydidehydro nucleosides showed moderate to potent anti-HCMV activity, but their bioisosteric thioapio dideoxydidehydro nucleosides did not exhibit any significant antiviral activity.

Syntheses and structure-activity relationships of novel apio and thioapio dideoxydidehydronucleosides as anti-HCMV agents

On the basis of the fact that apio dideoxynucleosides, in which the furanose oxygen and the C2 of the 2,3-dideoxyribose are transposed, exhibited potent anti-HIV activity and 2′,3′-dideoxy-2′,3′-didehydronucleosides also showed potent anti-HIV activity, we synthesized apio dideoxydidehydronucleosides in which the oxygen atom and the double bond of the 2,3-dideoxy-2,3-didehydroribose are exchanged. The thioapio dideoxydidehydronucleosides were also synthesized since sulfur serves as a bioisostere of oxygen. Apio dideoxydidehydronucleosides 13a-f were synthesized starting from 1,3-dihydroxyacetone, utilizing phenylselenenyl chemistry as a key step. The ratio of the anomeric mixture was variable from 1:1 to 5:1 during the condensation of nucleosidic bases with the phenylselenyl acetate 11 in the presence of a Lewis acid. This is in contrast with other glycosyl donors such as 5-O-(tert-butyldiphenylsilyl)-2-phenylselenenyl-2,3-dideoxyribosyl acetate which shows excellent neighboring group effect (α:β = 1:99). Thioapio dideoxydidehydronucleosides 22a,b were synthesized from the lactone 9 via thiolactone 17 as a key intermediate which was synthesized from dicyclohexylcarbodiimide coupling of the mercapto acid produced from the basic hydrolysis of thioacetate 16. The majority of apio analogues synthesized in this study exhibited moderate to potent anti-HCMV activity, among which the 5-fluorouracil derivative 13c was found to be the most potent against HCMV, while thioapio analogues showed no activity against HCMV. However, all synthesized compounds did not exhibit any significant activities against HIV-1, HSV-1, and HSV-2. The fact that apio dideoxydidehydronucleosides were active against HCMV suggests that the apio dideoxydidehydro sugar moiety can serve as a novel template for the development of new antiviral agents.

Total synthesis of (±)-Iso-d4T as potential antiviral agent

(±)-Iso-d4T which may act as a bioisostere of d4T was synthesized from 1,3-dihydroxyacetone using phenyl selenenium chemistry as a key step.