157761-58-5

Upstream product

• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 7177-79-9 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 73111-58-7 2,3,4-tri-O-benzyl-5,6-dideoxy-D-xylo-hex-5-enose 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 100-39-0 benzyl bromide 
• 185987-56-8 2-(R)-3-(S)-4-(R)-tribenzyloxy-5-t-butyldimethylsilyloxy-pentanal 
• 1335101-41-1 (3E,5E)-(1Ss)-(p-tolylsulfinyl)hepta-3,5-dien-2-one 
• 1335101-40-0 (S,3E,5E)-1-((S)-p-tolylsulfinyl)hepta-3,5-dien-2-ol 
• 119067-99-1 (-)-(1R,2R,3R,4S)-1-(hydroxymethyl)cyclohex-5-ene-2,3,4-triol 

Downstream Products

• 126661-83-4 cyclophellitol 

Relevant academic research and scientific papers

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

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.

Free Radical Studies and Solutions to the Synthesis of (+)-Cyclophellitol

D-Xylose serves as a starting material for approaches to the synthesis of the glucosidase inhibitors, (+)-cyclophellitol (1) and (+)-epi-cyclophellitol (2). An investigation of the cyclization of diastereomeric oxiranyl radicals to achieve this goal was m

Synthesis of new cyclitol derivatives

In recent years, an increasing interest in the synthesis of glycosidase inhibitors has been observed due to their biological properties. Glycosidase inhibitors can be classified in two distinct classes: reversible inhibitors (glycals, glyconolactones, glycosylamines, aminocyclitols, etc), and irreversible inhibitors (conduritol epoxides, 5,6-anhydro-1- deoxynojirimycine). Among the naturally occurring glycosidase inhibitors, cyclitol epoxides and aminocyclitols have been extensively studied due to their antibiotic properties. They have been synthesized from carbohydrate derivatives, endo-adducts of furan and acrylic acid or by chemoenzymatic conversion of aromatic derivatives. As part of our investigation on the synthesis of new potential enzyme inhibitors, we have recently prepared some new thiirane analogs. We also reported in a preliminary communication the synthesis of analogs of naturally occurring aminocyclitols. We now describe these previous results in further detail.

Synthesis of new aminocyclitols as potent enzymatic inhibitors

The syntheses of new pseudo-saccharides having an allylic amino moiety or an aziridine group are reported starting from methyl-α-D-glucopyranoside. To enhance the hydrophilic/lipophilic balance, pseudo-saccharides 9 and 10 were linked with a glycosyl deri