1941-50-0

Usage

Uses

Used in Organic Chemistry Research:
D-Arabinose diethyldithioacetal is used as a reagent for selectively protecting hydroxyl groups in carbohydrates during organic synthesis. This selective protection allows for the synthesis of complex molecules with greater ease and precision.
Used in Pharmaceutical Development:
D-Arabinose diethyldithioacetal is used in the preparation of various carbohydrate derivatives and pharmaceutical compounds. Its ability to protect hydroxyl groups makes it a valuable tool in the synthesis of complex drug molecules.
Used in the Synthesis of Nucleosides and Nucleotides:
D-Arabinose diethyldithioacetal serves as a building block for the synthesis of important compounds such as nucleosides and nucleotides, which are essential components of nucleic acids and have significant applications in molecular biology and medicine.
Used in the Protection of Hydroxyl Groups in Carbohydrate Derivatives:
D-Arabinose diethyldithioacetal is used as a protecting agent for hydroxyl groups in the synthesis of carbohydrate derivatives. This selective protection allows for the controlled formation of desired products and minimizes unwanted side reactions.

InChI:InChI=1/C9H20O4S2/c1-3-14-9(15-4-2)8(13)7(12)6(11)5-10/h6-13H,3-5H2,1-2H3

Upstream product

• 10323-20-3 D-Arabinose 
• 75-08-1 ethanethiol 
• 15397-09-8 D-glycero-D-talo-heptonic acid 4-lactone 
• 28697-53-2 D-arabinopyranose 

Downstream Products

• 13942-77-3 1-deoxy-D-arabinitol 
• 5329-46-4 O²,O³,O⁴-triacetyl-O⁵-trityl-D-arabinose-diethyldithioacetal 
• 5329-45-3 2,3,4,5-tetra-O-acetyl-D-arabinose diethyl dithioacetal 
• 91414-41-4 5-O-triphenylmethyl-D-arabinose diethyl dithioacetal 
• 103476-14-8 2,3,4,5-tetra-O-benzoyl-D-arabinose diethyl dithioacetal 
• 7151-04-4 5-O-benzoyl-D-arabinose diethyl dithioacetal 
• 103665-71-0 O⁵-(toluene-4-sulfonyl)-D-arabinose diethyl dithioacetal 
• 25129-51-5 methyl β-D-arabinofuranoside 
• 56607-40-0 methyl D-arabinofuranoside 
• 109428-97-9 (R),(R)-2,4:3,5-di-O-benzylidene-D-arabinose diethyl dithioacetal 
• 106450-92-4 R-3,5-O-benzylidene-D-arabinose diethyl dithioacetal 
• 13039-93-5 2,2:4,5-di-O-isopropylidene-D-arabinose 
• 162517-90-0 5-O-(tert-butyldiphenylsilyl)-D-arabinose diethyldithioacetal 
• 178455-69-1 2,3-(S):4,5-(R)-di-O-benzylidene-D-arabinose diethyl dithioacetal 

Relevant academic research and scientific papers

De novo synthesis of aceric acid and an aceric acid building block

The de novo synthesis of an aceric acid thioglycoside building block and the total synthesis of the plant carbohydrate aceric acid are described via a highly convergent strategy. Aldol reaction of acetaldehyde and a protected tartaric acid derivative provided the open chain carbohydrate. Subsequent acid treatment yielded the aceric acid thioglycoside in 35% total yield over five steps. Oxidative cleavage of the thioketal in the open chain carbohydrate and basic hydrolysis of the methyl ester furnished fully deprotected aceric acid in 31% yield over six steps.

Regioselective Synthesis of Difluorinated C-Furanosides Involving a Debenzylative Cycloetherification

A highly regioselective synthesis of valuable gem-difluorinated C-furanosides from unprotected aldoses via a debenzylative cycloetherification (DBCE) reaction induced by diethylaminosulfur trifluoride is descibed. The scope and limitations of this DBCE reaction are described using a series of commercially available pentoses and hexoses to afford, without selective protection/deprotection sequences, the corresponding gem-difluorinated C-furanosides in moderate to good yields.

Efficient and regioselective synthesis of γ-lactone glycosides through a novel debenzylative cyclization reaction

An efficient and regioselective approach for the construction of synthetically important γ-lactone glycosides is reported from unprotected aldoses through a new debenzylative lactonization (DBL) reaction. The scope and limitations of this DBL reaction are described starting from a series of commercially available hexoses (l-fucose, d-galactose, d-glucose) and pentoses (d-arabinose, d-ribose, d-lyxose, d-xylose) to afford the corresponding γ-lactones in good yields and without concomitant δ-lactone formation.

NEW ANTIBACTERIAL COMPOUNDS AND BIOLOGICAL APPLICATIONS THEREOF

The invention relates to compounds of formulae (Ia), (Ib) or (Ic) wherein, - A1 and A2, identical or different, are H, (C1-C6) alkyl, (C1-C6) fluoroalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkyl-ORa, (C1-C6) alkyl-SRa, (C1-C6) alkyl-NRaRb, ORa, SRa, NRaRb, or CORa; - A3 is H, OH or form a carbonyl with A4; - A4 is H, OH or form a carbonyl with A3; - A5 is H, CRaRbOH, F, OH or forms a double bond with X in the case where X is CH; - A6 is H or F; - X is CH2, CHF, CF2, CHOH, O, S, NRa or a simple bond, or X is CH in the case where A5 forms with X a double bond; - Y is P(O) (ORa) (ORb) or P (O) (ORa) (NRaRb); - V is O or S; - A7 is H, (C1-C6) alkyl, (C1-C6) fluoroalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl or (C1-C6) alkyl-ORa; - A8 is OH or H, - Ra and Rb, identical or different, are H, (C1-C6) alkyl, (C1-C6) fluoroalkyl, (C1-C6) alkyl-OH or (C1-C6) alkyl-O- (C1- C6) alkyl; and their addition salts thereof with acids and bases, their preparation and their use in the antibacterial prevention and therapy, used alone or in association with antibacterials, antivirulence agents or drugs reinforcing the host innate immunity.

On the synthesis of cepacin A

Efforts directed toward a total synthesis of cepacin A is presented in full detail. The C-7, C-8, and C-9 stereogenic centers in the target molecule were derived from d-arabinose. The configuration of the allene axis was controlled at the bromoallenation step by the C-10 configuration of the precursor. An unexpected yet very interesting phenomenon was observed with the bromoallenation, where the α-isomer of the propargylic alcohol 31 was entirely resistant to the conditions that worked so well for its β-counterpart. The problem was eventually solved by careful tuning of the size of the neighboring groups based on the clue obtained from conformational analysis. The diyne moiety was incorporated into the molecular framework through a coupling of the TMS protected diyne with a proper bromoallene under the Sonogashira conditions with EtOAc as the solvent. Use of other solvents at this step led to complete failure.

Studies on enolization of aldehydo-aldose derivatives

Acetylation of the 2,3-O-isopropylidene derivative (1) of d-glyceraldehyde with hot acetic anhydride in the presence of sodium acetate give a mixture of (Z)- and (E)-enol acetates (2 and 3), together with the acetylated racemic aldehydrol (4) of 1. Likewise, the acyclic aldehydo 2,3:4,5-diisopropylidene acetals of d- and l-arabinose, d-xylose, and d-ribose underwent conversion into enol acetates, with the (Z) isomers preponderating, and convertible photochemically into the corresponding (E) isomers. Under other conditions of acetylation, the aldehydo derivatives were converted into the corresponding aldehydrol diacetates.

LAULIMALIDE ANALOGS AND USES THEREOF

The present invention provides compounds having formula 1: (I) and pharmaceutically acceptable derivatives thereof, wherein R1-R10, q, t, X0, X1, A, B, D, E, G, J, K, L, M and Z are as described generally and in classes and subclasses herein, and additionally provides pharmaceutical compositions thereof, and methods for the use thereof for the treatment of disorders associated with cellular hyperproliferation.

A simple and practical synthetic protocol for thioacetalization of carbonyl compounds

Various aldehydes and ketones are smoothly converted to the corresponding acyclic and cyclic dithioacetals in very good yields by employing catalytic amount of acetyl chloride at room temperature under solvent-free conditions. Some of the major advantages of this procedure are its mild reaction conditions, highly efficient and selective, good yields, economically cheaper and compatible in the presence of a wide variety of other protecting groups.

Elucidation of the 2-C-methyl-D-erythritol 4-phosphate pathway for isoprenoid biosynthesis: Straightforward syntheses of enantiopure 1-deoxy-D-xylulose from pentose derivatives

Optically pure 1-deoxy-D-xylulose, a key metabolite for feeding experiments in the methylerythritol phosphate pathway for isoprenoid biosynthesis, is conveniently synthesised from 1,2-O-isopropylidene-α-D-xylofuranose or from D-arabinose. This renders lab

BIORATIONAL DESIGN OF HERBICIDES: SYNTHESIS OF INHIBITORS OF THE PFP ENZYME

Transition state and reaction coordinate analog inhibitors of the PFP enzyme were synthesized for the biorational design of herbicides.Some of the promising ones were scaled up and tested on whole plants.Open chain, aza and phosphonated analogs of fructose showed significant PFP inhibitory activity.