176380-10-2

Upstream product

• 201603-48-7 (3S,4R,5R,6S)-4,5,6-Tris-benzyloxy-3-vinyl-oct-7-enoic acid methyl ester 
• 1335101-40-0 (S,3E,5E)-1-((S)-p-tolylsulfinyl)hepta-3,5-dien-2-ol 
• 220564-16-9 (-)-(1R,2S,3S,4R)-2,3,4-tribenzyloxy-5-cyclohexene-1-ol 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 66222-29-5 tri-n-butylstannylmethyl iodide 
• 844901-87-7 (2R,3R,4R,5S)-3,4,5-tri(benzyloxy)-2-vinyl-6-hepten-1-ol 
• 118968-02-8 (1S)-(1,3/2,4)-1,2-dibenzyloxy-3-hydroxy-4-hydroxymethylcyclohex-5-ene 
• 1335101-41-1 (3E,5E)-(1Ss)-(p-tolylsulfinyl)hepta-3,5-dien-2-one 
• 119067-99-1 (-)-(1R,2R,3R,4S)-1-(hydroxymethyl)cyclohex-5-ene-2,3,4-triol 

Downstream Products

• 157761-58-5 ((1R,2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-7-oxabicyclo-[4.1.0]heptan-2-yl)methanol (+)-2,3,4-tri-O-benzylcyclophellitol 
• 126661-83-4 cyclophellitol 

Relevant academic research and scientific papers

Synthesis of Carba-Cyclophellitols: a New Class of Carbohydrate Mimetics

Cyclophellitol and cyclophellitol aziridine are potent and irreversible inhibitors of retaining β-glucosidases. They preferentially adopt a 4H3 half-chair conformation, thereby mimicking the substrate-transition-state conformation characteristic of retaining β-glucosidases. As a consequence, both compounds bind tightly to the enzyme active site, and attack of the catalytic nucleophile onto the epoxide/aziridine results in enzyme deactivation. Replacement of the epoxide oxygen in cyclophellitol by a (substituted) carbon yielded carba-cyclophellitols, a conceptually new class of inhibitors of retaining β-glucosidases, as we demonstrated in a recent communication. In this paper, in-depth synthetic studies of this class of compounds are described, and the preparation of a comprehensive set of structurally and configurationally new carba-cyclophellitols is presented.

Stereoselective Formal Synthesis of (+)- and (-)-Cyclophellitol and (-)-Conduritol-B and Synthesis of (-)-Conduramine-B Derivative Using a Sulfinyl Moiety for C-O Bond Formation and α-Chloro Sulfide for C-C Bond Formation

The formal total synthesis of both the enantiomers of cyclophellitol and conduritol-B and synthesis of conduramine-B derivative have been achieved from a common intermediate, obtained by regio- and stereoselective vicinal functionalization of a diene utilizing an intramolecular sulfinyl group as a nucleophile, followed by stereoselective preparation of an allylic sulfide by reaction of vinylzinc bromide with an electrophilic α-chloro sulfide, and last by ring-closing metathesis reaction as the key steps. The sulfoxide, sulfilimine, and sulfur ylid prepared from this common intermediate have been transformed into derivatives of conduritol-B, conduramine-B, and (-)-cyclophellitol, respectively. The silyl sulfide was converted via sila-Pummerer rearrangement, hydrolysis, and reduction in an one-pot operation to a hydroxymethyl group. [2,3]-Wittig-Still rearrangement was employed for the synthesis of (+)-cyclophellitol. The potential utility of sulfur intermediates as nucleophilic and electrophilic partners in total synthesis is elegantly demonstrated.

Synthesis and evaluation of hydroxymethylaminocyclitols as glycosidase inhibitors

Four series of C7N aminocyclitol analogues of glucose were synthesized by stereocontrolled epoxide opening of hydroxyl protected forms of the cyclohexane epoxides cyclophellitol and 1,6-epi-cyclophellitol. The resulting hydroxymethyl substitute

A novel chemo-multienzymatic synthesis of bioactive cyclophellitol and epi-cyclophellitol in both enantiopure forms

A new route to synthesize cyclophellitol and epi-cyclophellitol from racemic starting materials in enantiopure forms has been developed. The synthesis involves a multi-enzymatic biotransformation pathway of the novel cyano-cyclitol (1R,4S,5R,6R)/(1S,4R,5S

Enantiodivergent formal synthesis of (+)-and (-)-cyclophellitol from D-xylose based on the latent symmetry concept

(Chemical Equation Presented) Formal synthesis of (+)- and (-)-cyclophellitol from D-xylose has been accomplished through utilization of the latent plane of chirality present in the starting carbohydrate. The synthetic pathway is suitable for preparation

Conversion of D-Glucose to Cyclitol with Hydroxymethyl Substituent via Intramolecular Silyl Nitronate Cycloaddition Reaction: Application to Total Synthesis of (+)-Cyclophellitol

(Matrix presented). A diastereoisomeric mixture of 1-nitro-6-heptene-2,3,4, 5-tetraol derivative (A) was prepared by Henry reaction between D-glucose-based aldehyde and nitromethane. Only the (2S)-isomer of A led to cyclitol (B) via nitronate-olefin cyclo

AAA in KAT/DYKAT processes: First- and second-generation asymmetric syntheses of (+)- and (-)-cyclophellitol

Kinetic resolutions and kinetic asymmetric transformations (KAT) as well as dynamic kinetic resolutions and dynamic kinetic asymmetric transformations (DYKAT) are important synthetic protocols. The feasibility of KAT and DYKAT processes for asymmetric all

Pd catalyzed kinetic resolution of conduritol B. Asymmetric synthesis of (+)-cyclophellitol

Enantiomerically pure (+)-cyclophellitol is readily available from benzoquinone employing an asymmetric palladium catalyzed kinetic resolution of racemic conduritol B and a novel easily cleavable pivalate analogue.