124600-99-3

Basic information

• Product Name: (4S,5S)-2-bromo-1,3-bis[(4-methylphenyl)sulfonyl]-4,5-diphenyl-1,3,2-diazaborolidine
• Synonyms: (4S,5S)-2-bromo-1,3-bis[(4-methylphenyl)sulfonyl]-4,5-diphenyl-1,3,2-diazaborolidine
• CAS NO: 124600-99-3
• Molecular Weight: 609.372
• Mol File: 124600-99-3.mol

Chemical Properties

• CAS DataBase Reference: (4S,5S)-2-bromo-1,3-bis[(4-methylphenyl)sulfonyl]-4,5-diphenyl-1,3,2-diazaborolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5S)-2-bromo-1,3-bis[(4-methylphenyl)sulfonyl]-4,5-diphenyl-1,3,2-diazaborolidine(124600-99-3)
• EPA Substance Registry System: (4S,5S)-2-bromo-1,3-bis[(4-methylphenyl)sulfonyl]-4,5-diphenyl-1,3,2-diazaborolidine(124600-99-3)

Safety Data

• Hazardous Substances Data: 124600-99-3(Hazardous Substances Data)

Upstream product

• 10294-33-4 boron tribromide 
• 170709-41-8 (1S,2S)-N,N'-bis((4-methylphenyl)sulfonyl)-1,2-diphenylethane-1,2-diamine 
• 121758-19-8 4-methyl-N-((1R,2R)-2-{[(4-methylphenyl)sulfonyl]amino}-1,2-diphenylethyl)benzenesulfonamide 

Downstream Products

• 124563-11-7 (S)-nona-1,2-dien-4-ol 
• 121758-23-4 C₃₁H₃₀BBrN₂O₄S₂ 
• 109907-84-8 (S)-1-cyclohexyl-buta-2,3-dien-1-ol 
• 124563-28-6 (S)-1-Cyclohexyl-2-ethyl-buta-2,3-dien-1-ol 

Relevant articles and documents

Method for synthesis of gamma-lactone by asymmetric aldol reaction by kinetic resolution

The present invention relates to a method for synthesizing gamma-lactone by an asymmetric aldol reaction through kinetic division. More particularly, by acquiring an enantiomer from a mixture as a method using a difference in speed of a racemic mixture, the present invention can be efficiently used for the synthesis of gamma-lactone and xylocolactone in terms of cost and time.COPYRIGHT KIPO 2021

Kinetic Resolution of Racemic Aldehydes through Asymmetric Allenoate γ-Addition: Synthesis of (+)-Xylogiblactone A

A synthesis of (+)-xylogiblactone A has been achieved from t-butyl 2-methylbuta-2,3-dienoate in a linear three-step sequence. The key elements of the synthesis include a kinetic resolution of racemic 2-silyoxyaldehyde through the allenoate γ-addition to y

A Regulation of Regiodivergent Routes for Enantioselective Aldol Addition of 2-Alkyl Allenoates with Aldehydes: α-Addition versus γ-Addition

A method for the regioselective asymmetric aldol addition of 2-alkyl allenoates with aldehydes to provide an α- or γ-adduct depending on the aldehyde pair is reported. In most cases, except enals, a mixture of a chiral bromoborane with 2-alkyl allenoates in the presence of iPr2NEt can react with aldehydes to provide efficient γ-addition products as single isomers containing axial and central chirality. On the other hand, observations indicate that enals undergo α-addition to yield highly functionalized adducts, including an α-carbon quaternary center in high levels of diastereo- and enantioselectivity.

Concise Total Synthesis of Enigmazole A

An efficient entry into the phosphorylated marine macrolide enigmazole A is described. Enigmazole A interferes with c-Kit signaling by an as yet unknown mode of action and is therefore a potential lead in the quest for novel anticancer agents. Key to succ

Elaboration of Sterically Hindered δ-Lactones through Ring-Closing Metathesis: Application to the Synthesis of the C1-C27 Fragment of Hemicalide

The synthesis of the C1-C27 fragment of hemicalide, a marine metabolite displaying a unique potent antiproliferative activity, has been accomplished. The synthetic approach highlights a remarkably efficient ring-closing metathesis reaction catalyzed by Nolan ruthenium indenylidene complexes to elaborate the highly substituted δ-lactone framework.

Asymmetric aldol reaction of allenoates: Regulation for the selective formation of isomeric allenyl or alkynyl aldol adduct

A highly stereoselective synthesis of 3-butynyl-threo-aldol adducts is achieved from the reaction of allyl allenoate with a chiral bromoborane in the presence of iPr2NEt, followed by addition of BF3·OEt2 as an additive to

Stereocontrol in asymmetric SE' reactions of γ-substituted α,β-unsaturated aldehydes

Asymmetric SE' reactions of (E)-and (Z)-γ-substituted-α,β- unsaturated aldehydes have been studied for the stereocontrolled preparation of nonracemic alcohols. Mild exchange reactions of allylic stannanes provide access to chiral 1,3-bis-(tolylsulfonyl)-4

A bidirectional SE′ strategy for 1,5- syn and 1,5- anti stereocontrol toward the synthesis of complex polyols

Studies report a bidirectional SE′ strategy applicable for the stereocontrolled synthesis of nonracemic 1,5-syn and 1,5-anti diols and their derivatives. Nonracemic 1,3,2-diazaborolidine auxiliaries are incorporated by chemoselective tin-boron exchange to provide reactive allylic boranes. The convergent pathway utilizes sequential reactions with two aldehydes producing stereochemical outcomes from cyclic, closed, and open transition state preferences, respectively. Synthesis of fragment 16 of peloruside A is accomplished in four steps from readily available aldehydes 9 and 13.

A novel allylic transfer reaction of chirally modified 2-borylbutadiene: Synthesis of chiral homoallenyl alcohols

An enantioselective synthesis of the homoallenyl alcohols was achieved from the reaction of chiral 2-borylbutadiene with aldehydes through an allylic transfer reaction in good yields and enantioselectivities. The Royal Society of Chemistry.

Studies for the enantiocontrolled preparation of substituted tetrahydropyrans: Applications for the synthesis of leucascandrolide A macrolactone

Strategies for the stereocontrolled preparations of 2,6-cis- and 2,6-trans-substituted tetrahydropyrans have been devised. These studies have explored methodology for asymmetric induction in SE′ reactions using chiral 1,3,2-diazaborolidine controllers. Reactions with aldehydes at -78°C yield nonracemic 1,5-diols for chemoselective internal backside displacements. This concept is developed as a flexible and reliable strategy in studies toward leucascandrolide A macrolactone 2 via the sequential applications of SE′ reactions leading to the C1-C9 aldehyde 14, and the bis-tetrahydropyran 59, respectively.