160401-04-7

Upstream product

• 5336-08-3 D-Ribono-1,4-lactone 
• 160343-86-2 <1R-(1α,2β,3β,4β,5β)>-5-Amino-1,1':2,3-bis(isopropylidenedioxy)-1-methylcyclopentan-4-ol 
• 160531-14-6 3,4-O-Isopropylidene-aldehydo-L-ribo-penturono-5,2-lactone 
• 160343-81-7 <1R-(1α,2α,3α,4α,5α)>-4-<(Benzyloxycarbonyl)oxy>-1-<<(tert-butyldimethylsilyl)oxy>methyl>-2,3-(isopropylidenedioxy)-6-oxabicyclo<3.1.0>hexane 
• 160343-80-6 <1S-(1α,4α,5α)>-1-<(Benzyloxycarbonyl)oxy>-3-<<(tert-butyldimethylsilyl)oxy>methyl>-4,5-(isopropylidenedioxy)-2-cyclopentene 
• 160343-96-4 <1R-(1α,2β,3β,4β,5β)>-5-Azido-1,1':2,3-bis(isopropylidenedioxy)-1-methylcyclopentan-4-ol 
• 160401-03-6 <1R-(1α,2β,3β,4β,5β)>-5-Azido-1-(hydroxymethyl)-2,3-(isopropylidenedioxy)-1,4-cyclopentanediol 
• 160343-77-1 (Z)-5-O-(tert-Butyldimethylsilyl)-4,5-didehydro-2,3-O-isopropylidene-D-erythro-penturono-1,4-lactone 
• 160343-78-2 (3aR,6aR)-6-{{[(1,1-dimethylethyl)dimethylsilyl]oxy}methyl}-3a,6a-dihydro-2,2-dimethyl-4H-cyclopenta[d]-1,3-dioxol-4-one 
• 160343-79-3 (3aS,4S,6aR)-6-{{[(1,1-dimethylethyl)dimethylsilyl]oxy}methyl}-3a,6a-dihydro-2,2-dimethyl-4H-cyclopenta[d]-1,3-dioxol-4-ol 
• 30725-00-9 2,3-O-isopropylidene-D-ribonic-γ-lactone 
• 207516-12-9 Acetic acid (1S,2R,3R,4R,5S)-2,3-diacetoxy-5-((S)-2-acetoxy-2-phenyl-acetylamino)-4-benzyloxymethyl-cyclopentyl ester 
• 207516-21-0 Acetic acid (1R,2S,3S,4S,5R)-2,3,4-triacetoxy-1-acetoxymethyl-5-phenylacetylamino-cyclopentyl ester 
• 207516-15-2 Acetic acid (1S,2R,3R,4R,5S)-2,3-diacetoxy-4-hydroxymethyl-5-phenylacetylamino-cyclopentyl ester 

Downstream Products

• 160868-00-8 (3aR,4R,5S,6R,6aS)-4-Hydroxymethyl-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylamino)-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazole-4,5,6-triol 

Relevant academic research and scientific papers

Enantioselective approaches to aminocyclopentitols: A total synthesis of (+)-6-epitrehazolin and a formal total synthesis of (+)-trehazolin

Potent inhibitors of trehalase, such as trehazolin and its congeners, represent an attractive approach to the design of effective new insect control agents. In this report, enantioselective total syntheses of (-)-6- epitrehazolin and (+)-trehazolin were achieved using the asymmetric heterocycloaddition between [(benzyloxy)methyl]cyclopentadiene and the acylnitroso compound arising from in situ oxidation of (S)-mandelohydroxamic acid with tetrabutylammonium periodate. Further functionalization of the resulting 3,4,5-trisubstituted cyclopentene, either involving osmylation or epoxidation of the double bond, efficiently created pentasubstituted cyclopentanes. Introduction of the quaternary carbon in both synthesis targets was achieved via stereoselective osmylation of an intermediate 2,3,4,5-substituted 1-methylenecyclopentane.

Stereocontrolled syntheses of 6-epi-trehazolin and 6-epi-trehalamine from D-ribonolactone

6-epi-Trehazolin was synthesized in a stereocontrolled manner, and this synthesis proved that an oxazine structural isomer of 6-epi-trehazolin does not exist.