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(-)-B-Methoxydiisopinocampheylborane

Catalog Number
ACM85134981-1
Product Name
(-)-B-Methoxydiisopinocampheylborane
Structure
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CAS
85134-98-1
  • Product Overview
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Synonyms
(-)-B-Methoxydiisopinocampheylborane;(+)-B-Methoxydiisopinocampheylborane;85134-98-1;PubChem18146;PubChem18153;IAQXEQYLQNNXJC-NQWKWHCYSA-N;99438-28-5;ZINC170159722;Methoxybis[(1alpha,5alpha)-2beta,6,6-trimethylbicyclo[3.1.1]heptane-3alpha-yl]borane;
IUPAC Name
methoxy-bis[(1R,2S,3R,5R)-2,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]borane;
Molecular Weight
316.336g/mol
Molecular Formula
C21H37BO;
Canonical SMILES
B(C1CC2CC(C1C)C2(C)C)(C3CC4CC(C3C)C4(C)C)OC;
InChI
InChI=1S/C21H37BO/c1-12-16-8-14(20(16,3)4)10-18(12)22(23-7)19-11-15-9-17(13(19)2)21(15,5)6/h12-19H,8-11H2,1-7H3/t12-,13-,14+,15+,16-,17-,18-,19-/m1/s1;
InChI Key
IAQXEQYLQNNXJC-NQWKWHCYSA-N;
Storage
2-8°C
Complexity
442
Covalently-Bonded Unit Count
1
Defined Atom Stereocenter Count
8
Exact Mass
316.294g/mol
H-Bond Acceptor
1
Heavy Atom Count
23
Monoisotopic Mass
316.294g/mol
Rotatable Bond Count
3
Topological Polar Surface Area
9.2A^2
Application
(-)-B-Methoxydiisopinocampheylborane is a versatile chiral catalyst employed in synthetic organic chemistry to facilitate various complex reactions. Its primary purpose is to aid in the creation of intricate natural products and other compounds, such as homoallylic alcohols, by serving as an intermediate in various synthetic processes. This compound is involved in critical reactions, including oxidative cyclization and alkylation for ionomycin synthesis, intramolecular conjugate additions for producing tetrahydropyrans, aldol additions, Suzuki couplings, and allylation. Additionally, it plays a vital role in synthesizing macrolides like (-)-Lyngbyaloside B, noted for their antiproliferative activities, highlighting its importance in medicinal chemistry and drug development.
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