56196-34-0

Upstream product

• 69247-19-4 isopropyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 
• 67-63-0 isopropyl alcohol 
• 2873-29-2 D-glucal triacetate 
• 171228-22-1 isopropyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranoside 
• 65914-22-9 1,4,6-Tri-O-acetyl-α,β-D-erythro-hex-2-enopyranose (Pseudo-C-glucal triacetate) 

Downstream Products

• 102795-07-3 (S)-6-((S)-2-Benzenesulfonyl-1-methyl-ethyl)-3,6-dihydro-pyran-2-one 
• 102795-06-2 Acetic acid (2R,3S)-2-((S)-2-benzenesulfonyl-1-methyl-ethyl)-6-oxo-3,6-dihydro-2H-pyran-3-yl ester 
• 102795-02-8 (2R,3S,6S)-2-((E)-2-Benzenesulfonyl-2-trimethylsilanyl-vinyl)-6-isopropoxy-3,6-dihydro-2H-pyran-3-ol 
• 102795-05-1 Acetic acid (2R,3S,6S)-2-((S)-2-benzenesulfonyl-1-methyl-ethyl)-6-hydroxy-3,6-dihydro-2H-pyran-3-yl ester 
• 102795-04-0 Acetic acid (2R,3S,6S)-2-((S)-2-benzenesulfonyl-1-methyl-ethyl)-6-isopropoxy-3,6-dihydro-2H-pyran-3-yl ester 

Relevant academic research and scientific papers

Structure-based design, synthesis and antitumoral evaluation of enulosides

Enulosides, carbohydrate derivatives containing an α,β-unsaturated carbonyl unit, were designed and obtained in high yields and isomeric purity. All synthesized compounds exhibited antitumoral activity in micromolar range against four tested tumor cells lines, being the best results observed for HL-60?cells. These compounds open new possibilities to prepare an array of more active, site-specific or selective antitumor agents. 2016 Elsevier Ltd. All rights reserved.

2,3-Dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents: Design, synthesis, biological evaluation and SAR studies

The alarming resurgence of tuberculosis (TB) underlines the urgent need for development of new and potent anti-TB drugs. Towards this goal we herein report the design and synthesis of 2,3-dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercula

C-3 alkyl/arylalkyl-2,3-dideoxy hex-2-enopyranosides as antitubercular agents: Synthesis, biological evaluation, and QSAR study

A series of C-3 alkyl and arylalkyl 2,3-dideoxy hex-2-enopyranoside derivatives were synthesized by Morita - Baylis-Hillman reaction using enulosides 4, 5, and 6 and various aliphatic and aromatic aldehydes. The compounds were evaluated in vitro for the c

The chiron approach to pironetins: Synthesis of the δ-lactonic fragment and modified building blocks from D-glucal

The synthesis of the δ-lactonic fragment of pironetin (1), a natural product with outstanding antimitotic properties, is reported. The synthesis was achieved from commercially available tri-O-acetyl-D-glucal (6) that was employed as starting material for

TRANSACETALISATION PROCESS

The invention relates to the resolution of racemic mixtures, and in particular to the separation of enantiomers of chiral alcohols utilising recyclable chiral auxiliaries. The present invention also relates to a process for preparing these recyclable chiral auxiliaries using an enantiomerically pure alcohol.

Synthesis of JKLM ring fragment of ciguatoxin via acetylene-cobalt strategy

A stereoselective synthesis of the JKLM ring fragment has been achieved through a coupling between two segments via heteroconjugate addition, seven-membered ether ring formation mediated by an acetylene cobalt complex and spiroketalization reaction.

Convergent synthesis of the E′FGH ring fragment of ciguatoxin 1B via an acetylene cobalt complex strategy

A convergent synthesis of the E'FGH ring fragment 28 of ciguatoxin 1B, a principal toxin causing widespread seafood poisonings "ciguatera", has been accomplished through (i) coupling between the E' ring-acetylide 9 and the H ring-aldehyde 20, (ii) stereoselective F ring cyclization via an acetylene cobalt complex, (iii) conversion to a carbonyl function under high-pressure hydrogenation, and (iv) reductive hydroxyketone cyclization to construct the G ring. In the 1H NMR analysis of 28 at room temperature, a considerable broadening phenomenon was observed due to the slow conformational changes of the FG ring, as reported for natural ciguatoxin 1B. When measured in pyridine at -20 °C, the spectra of 28 exhibited a 3.5:1 mixture of two conformational isomers (UP and DOWN conformers).

Synthesis of the JKLM-ring fragment of ciguatoxin

A stereoselective synthesis of the LM-ring fragment has been achieved starting from a sugar derivative. A stereoselective synthesis of the JKLM-ring fragment has been achieved through a coupling between two segments via heteroconjugate addition, seven-membered ether ring formation mediated by an acetylene cobalt complex, and spiroketalization reaction.

Mirror image synthesis left ends of ciguatoxin and gambiertoxin 4b

Three compounds related to the AB fragments of ciguatoxin and gambiertoxin 4b and two diastereomers (at the C-2 position) of the ABC fragment of ciguatoxin have been synthesized in enantiomeric form. The stereochemistry of the C-2 position was introduced selectively from the corresponding pentose derivative. Construction of the A ring with its side chain was completed by Nicholas type cyclization of an acetylene bis(cobalthexacarbonyl) complex followed by reductive decomplexation.

Absolute stereostructure of callystatin A, a potent cytotoxic polyketide from the marine sponge, Callyspongia truncata

The unidentified configurations at C5 and C10 incallystatin A (1), a potent cytotoxic polyketide from the marine sponge Callyspongia truncata, were determined to be R,R by comparing the circular dichroism spectrum of 1 with those of two model compounds 2 and 3. Compounds 2 and 3 were synthesized by using E-selective Wittig olefination at the C6-C7 position as a key reaction.