133268-20-9

Upstream product

• 100-39-0 benzyl bromide 
• 17401-06-8 (2S,3S)-1,4-bis(benzyloxy)-2,3-butanediol 
• 68394-39-8 (2S,3S)-(-)-bis(dibenzyloxymethyl)-2,2-dimethyl-1,3-dioxolane 
• 91538-88-4 C₃₂H₃₄O₈S₂ 
• 17137-55-2 (2S,3S)-2,3-di(methanesulfonyloxy)-1,4-dibenzyloxybutane 

Downstream Products

• 109582-31-2 (2S,3S)-1,4-bis(phenylmethoxy)-2,3-diaminobutane 
• 1036322-95-8 C₁₈H₁₆N₆O₄ 
• 139951-79-4 (2S,3S)-2,3-Bis-benzyloxymethyl-piperazine 
• 139951-80-7 (2S,3S)-2,3-Bis-benzyloxymethyl-1,4-diaza-bicyclo[2.2.2]octane 
• 139951-78-3 (5S,6S)-5,6-Bis-benzyloxymethyl-piperazine-2,3-dione 
• 890662-56-3 (2S,3S)-1,4-dibenzyloxy-2,3-bis(2-pyridinoylamino)butane 
• 191354-85-5 (2S,3S)-1,4-dibenzyloxy-2,3-bis(benzoylamino)butane 
• 151630-98-7 (2S,3S)-1,4-dihydroxy-2,3-diaminobutane 

Relevant academic research and scientific papers

New supramolecular host systems, 11. The stereoisomeric diaminobutanediol and dioxadiazadecalin systems: Synthesis, structure, stereoelectronics, and conformation - Theory vs. experiment

We present new approaches to the (C2) chiral and meso 1,4-diamino-2,3- butanediol (1) and 2,3-diamino-1,4-butanediol (2) and derivatives. Reactions of these compounds with aldehydes to form the novel 1,5-dioxa-3,7- diazadecalin (DODAD) and 1,5-diaza-3,7-dioxadecalin (DADOD) classes of compounds (7, 9, 11-15) are also reported. These reactions are diastereospecific, i e, erythro (meso) or threo starting compounds lead to trans or cis products, respectively. The structural, conformational, and stereoelectronic aspects of these systems were probed experimentally and computationally and provided excellent insight into their properties and behaviour. Good agreement was observed between X-ray, NMR, and calculated results of the N,N'-dibenzyl derivatives of trans-DODAD (14) and trans-DADOD (15).

Efficient synthesis of (2R,3R)- and (2S,3S)-2,3-diaminobutane-1,4-diol and their dibenzyl ethers

(2R,3R)-2,3-Diaminobutane-1,4-diol 6 and its dibenzyl ether 7 were efficiently synthesized starting from L-tartaric acid 1a. The crucial step, debenzylation of intermediate dibenzyloxydiazide 4, was accomplished in good yield by boron trichloride-dimethyl sulfide complex. The enantiomeric series was similarly obtained starting from D-tartaric acid.

Synthesis of chiral 2,3-disubstituted 1,4-diazabicyclo [2.2.2] octane. New ligand for the osmium-catalyzed asymmetric dihydroxylation of olefins

Chiral 2,3-disubstituted 1,4-diazabicyclo[2.2.2]octane (DABCO) derivatives have been synthesized and utilized as a chiral ligand for the osmium-catalyzed asymmetric dihydroxylation of olefins. Optically active diols in up to 41%ee are obtained in good yields.

HYDROGEN AZIDE-AMINE SYSTEMS AS AN AZIDE NUCLEOPHILE FOR SUBSTITUTIONS OF SULFONATES, HALIDES, AND VICINAL DISULFONATES

Hydrogen azide-alkylamine combination turned out to ensure the displacement of simple primary or secondary sulfonates, halides, and vicinal disulfonates with an azido-group in which an enhanced reactivity is generally achieved as compared with a case of traditional alkali metal azides.