199185-03-0

Basic information

• Product Name: (4R,5R)-2-((E)-Hept-1-enyl)-4,5-bis-(methoxy-diphenyl-methyl)-[1,3,2]dioxaborolane
• Synonyms: (4R,5R)-2-((E)-Hept-1-enyl)-4,5-bis-(methoxy-diphenyl-methyl)-[1,3,2]dioxaborolane
• CAS NO: 199185-03-0
• Molecular Weight: 560.541
• Mol File: 199185-03-0.mol

Chemical Properties

• CAS DataBase Reference: (4R,5R)-2-((E)-Hept-1-enyl)-4,5-bis-(methoxy-diphenyl-methyl)-[1,3,2]dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,5R)-2-((E)-Hept-1-enyl)-4,5-bis-(methoxy-diphenyl-methyl)-[1,3,2]dioxaborolane(199185-03-0)
• EPA Substance Registry System: (4R,5R)-2-((E)-Hept-1-enyl)-4,5-bis-(methoxy-diphenyl-methyl)-[1,3,2]dioxaborolane(199185-03-0)

Safety Data

• Hazardous Substances Data: 199185-03-0(Hazardous Substances Data)

Upstream product

• 628-71-7 1-Heptyne 
• 220156-18-3 (4R,5R)-4,5-Bis-(methoxy-diphenyl-methyl)-[1,3,2]dioxaborolane 
• 130874-89-4 (2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenyl-2,3-butandiol 
• 60595-37-1 (E)-1-iodohept-1-ene 
• 1044871-05-7 (4'R,5'R,1E)-1-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]-3-chloro-2-propene 
• 199185-13-2 (4R,5R)-4,5-Bis-(methoxy-diphenyl-methyl)-2-((1S,2S)-2-pentyl-cyclopropyl)-[1,3,2]dioxaborolane 
• 130888-43-6 (4R,5R)-4,5-bis(methoxymethyl)-2-(p-methoxyphenyl)-α,α,α',α'-tetraphenyl-1,3-dioxolane 

Downstream Products

• 199185-13-2 (4R,5R)-4,5-Bis-(methoxy-diphenyl-methyl)-2-((1S,2S)-2-pentyl-cyclopropyl)-[1,3,2]dioxaborolane 
• 130874-89-4 (2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenyl-2,3-butandiol 
• 220156-18-3 (4R,5R)-4,5-Bis-(methoxy-diphenyl-methyl)-[1,3,2]dioxaborolane 
• 220156-28-5 (4R,5R)-2-hydroxy-4,5-bis[methoxy(diphenyl)methyl]-1,3,2-dioxaborolane 
• 251956-33-9 (4R,5R)-2-[(E)-2-{hydroxymethyl}ethenyl]-4,5-bis[methoxy(diphenyl)methyl]-1,3,2-dioxaborolane 
• 321882-78-4 (4R,5R,1'R,2'R)-2-[2-(hydroxymethyl)cyclopropyl]-4,5-bis[methoxy(diphenyl)methyl]-1,3,2-dioxaborolane 
• 199185-05-2 (4R,5R)-2-((E)-Hex-1-enyl)-4,5-bis-(methoxy-diphenyl-methyl)-[1,3,2]dioxaborolane 
• 199185-09-6 (4R,5R)-4,5-Bis-(methoxy-diphenyl-methyl)-2-((E)-styryl)-[1,3,2]dioxaborolane 
• 199185-21-2 (1'R,2'R,4R,5R)-4,5-bis(methoxydiphenylmethyl)-2-(2'-phenylcyclopropyl)-1,3,2-dioxaborolane 
• 220156-24-1 (4R,5R)-2-[(E)-2-[3-tert-butyl(dimethyl)siloxymethyl]ethenyl]-4,5-bis[methoxy(diphenyl)methyl]-1,3,2-dioxaborolane 
• 220156-26-3 (4R,5R)-2-[(E)-2-[3-tert-butyl(diphenyl)siloxypropyl]ethenyl]-4,5-bis[methoxy(diphenyl)methyl]-1,3,2-dioxaborolane 

Relevant articles and documents

Enantioselective Catalysts for the Synthesis of α-Substituted Allylboronates - An Accelerated Approach towards Isomerically Pure Homoallylic Alcohols

The use of a convenient protecting group for boronates allows a selective, catalyzed SN2′ reaction to generate allylboronates which are applied for the synthesis of enantiomerically pure homoallylic alcohols. Depending on the configuration of both catalyst and the protecting group any of the four possible stereoisomers can be formed. The rationale behind the selective addition is supported by density functional theory calculations.

Synthesis of enantiomerically pure cyclopropanes from cyclopropylboronic acids

A general method for the stereocontrolled synthesis of cyclopropanes is described. Various, highly stable, enantiomerically pure alkenylboronic esters 13 have been conveniently synthesized by the direct hydroboration of alkynes 11 using the new chiral 1,3,2-dioxaborolane 15. The high stability was also demonstrated by the selective deprotection of a tert- butyldimethylsilyl protecting group without hydrolyzing the boronic ester. The diastereoselective cyclopropanation of the olefins was achieved by the palladium(II) acetate catalyzed decomposition of diazomethane. This process was optimized giving cyclopropylboronic esters 20/21 in high yield (89-99%) and with good to excellent diastereomeric ratios (up to 95:5). The diastereomers were separated by means of MPLC and their configurations determined by X-ray crystallography (compound 21c), by transformation to known cyclopropanols, and by correlation of NMR data. Treatment with LiAlH4 followed by acidic hydrolysis yielded the enantiomerically pure cyclopropylboronic acid 27 for the first time and allowed the nearly quantitative recovery of the chiral auxiliary 3. Different protocols for the Suzuki coupling reaction of compound 27 were investigated.