74839-83-1

Usage

Uses

Used in Pharmaceutical Synthesis:
(2S,3S)-(-)-2,3-BUTANEDIOL DI-P-TOSYLATE is used as a reagent in the synthesis of pharmaceuticals for its versatile reactivity and stereochemical properties.
Used in Organic Synthesis:
(2S,3S)-(-)-2,3-BUTANEDIOL DI-P-TOSYLATE is used as a reagent in organic synthesis for its ability to participate in various types of reactions, such as oxidation and reduction.

InChI:InChI=1/C18H22O6S2/c1-13-5-9-17(10-6-13)25(19,20)23-15(3)16(4)24-26(21,22)18-11-7-14(2)8-12-18/h5-12,15-16H,1-4H3/t15-,16-/m1/s1

Upstream product

• 6982-25-8 d,l-2,3-butanediol 
• 98-59-9 p-toluenesulfonyl chloride 
• 24347-58-8 (R,R)-2,3-butandiol 
• 19132-06-0 (2S,3S)-butane-2,3-diol 
• 135638-22-1 <2R-(2α(2S*,3S*),3aα,4α,7α,7aα)>-3-<(Octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>-2-butanol 

Downstream Products

• 1450903-80-6 (2R,3R)-bis(2-iodo-3-nitrophenoxyl)butane 
• 74839-84-2 (R,R)-chiraphos 

Relevant academic research and scientific papers

Enantiomeric recognition of amino acid salts by macrocyclic crown ethers derived from enantiomerically pure 1,8,9,16-tetrahydroxytetraphenylenes

Asymmetric synthesis of (R,R)- and (S,S)-1,8,9,16- tetrahydroxytetraphenylenes was achieved from starting material (2R,3R)-butane-2,3-diol and (2S,3S)-butane-2,3-diol respectively by utilizing a center-to-axis strategy. A series of crown ether compounds 20, 24, and 25 and their corresponding enantiomers derived from chiral tetrahydroxytetraphenylene were synthesized in enantiomerically pure forms. Enantiomeric recognition properties of these hosts toward l- and d-amino acid methyl ester hydrochloride were studied by the UV spectroscopy titration. The tetramer hosts (S,S,S,S,S,S,S,S)-20 and (R,R,R,R,R,R,R,R)-20 exhibited the best enantioselectivities toward l- and d-alanine methyl ester hydrochloride salt with KL/KD = 4.1 and KD/KL = 3.9, respectively. The new chiral macrocyclic hosts would further enrich the host-guest chemistry.

Highly Active and Selective Ethylene Oligomerization Catalyst and Method of Preparing Hexene or Octene Using the Same

This invention relates to a chromium complex compound for selective ethylene oligomerization including a chiral ligand, and to a method of selectively preparing 1-hexene or 1-octene from ethylene using the same.

Pheromones, III: A Simple Method to Direct the Reduction of α-Alkoxy-carbonyl Compounds

Enantiomerically pure 1,2-diols bearing optionally syn or anti configurated secondary hydroxylic groups are synthesized from acetal-protected cyanohydrins.After resolution of the diastereomers the cyanohydrins are converted into α-alkoxy-ketones by Grignard-reaction followed by reduction using common chelating or non-chelating agents.Among others syntheses of enantiomerically pure pheromones, endo-Brevicomin, exo-Brevicomin and Dispalure are given as examples.

SYNTHESIS OF OPTICALLY PURE COMPOUNDS BY ENANTIOTOPICALLY DIFFERENTIATING MONOACETALIZATION OF PROCHIRAL DIKETONES. PART II. FRAGMENTATION OF β-KETO-ACETALS

Treatment of β-keto-acetals, derived from non-enolisable β-diketones, with sulfonic acids in boiling benzene results in a smooth retro-Claisen-type fragmentation.The acetal-C-atom is thereby transformed into a carboxylic ester via a dialkoxycarbenium ion, which is dealkylated by the sulfonate counter-ion.Application of this reaction to the diastereomeric monoacetals 3 and 4, derived from cis-9-methyl-decalin-1,8-dione (1), followed by transesterification with CH3OH, yields optically pure 4-(2'-methyl-3'-oxocyclohexyl)butyrate 9 ((+)-9 from 3, (-)-9 from 4) and the monosulfonate of meso-2,3-butanediol (-)-13 (Scheme 2).Unexpected, this cleavage proceeds as well with monoacetal 26, obtained by acetalization of trans-9-methyl-decalin-1,8-dione (27) with 2,2-dimethyl-1,3-propanediol (Scheme 7).Some attempts, aiming at an isomerization of the cis- and trans-decalin derivatives 3 and 24, or 25 and 26, via the postulated carboxonium intermediate, were not successful.

A New Chiral Rhodium(I) Complex of (2R,3R)-2,3-Bis(diphenylphosphino)butane for Asymmetric Hydrogenations

Rhodium(I) complexes of the new chiral ligand (2R,3R)-2,3-bis(diphenylphosphino)butane (4) - which is easily prepared from natural tartaric acid - hydrogenate α-(acylamino)acrylic acids to natural (S)-acylamino acids in high chemical (95-100percent) and optical (80-100percent) yields.