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(-)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane

Catalog Number
ACM93379487
Product Name
(-)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane
Structure
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CAS
93379-48-7
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Synonyms
[(4R,5R)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl]bis(diphenylmethanol); (4R,5R)-(-)-2,2-Dimethyl-alpha,alpha,alpha',alpha'-tetraphenyl-1,3-dioxolane-4,5-dimethanol, (R,R)-TADDOL; AKOS015895700; (-)-TRANS-ALPHA,ALPHA'-(DIMETHYL-1,3-DIOXOLANE-4,5-DIYL)BIS(DIPHENYLMETHANOL); SCHEMBL2504692; (-)-2,3-O-Isopropylidene-1,1,4,4-tetraphenyl-L-threitol; (4R,5R)-2,2-Dimethyl-alpha, alpha, alpha', alpha'-tetraphenyldioxolane-4,5-dimethanol; 1,3-Dioxolane-4,5-dimethanol, 2,2-dimethyl-alpha4,alpha4,alpha5,alpha5-tetraphenyl-, (4R,5R)-; FT-0604376; CD-566;
IUPAC Name
[(4R,5R)-5-[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-diphenylmethanol;
Molecular Weight
466.577g/mol
Molecular Formula
C31H30O4;
Canonical SMILES
CC1(OC(C(O1)C(C2=CC=CC=C2)(C3=CC=CC=C3)O)C(C4=CC=CC=C4)(C5=CC=CC=C5)O)C;
InChI
InChI=1S/C31H30O4/c1-29(2)34-27(30(32,23-15-7-3-8-16-23)24-17-9-4-10-18-24)28(35-29)31(33,25-19-11-5-12-20-25)26-21-13-6-14-22-26/h3-22,27-28,32-33H,1-2H3/t27-,28-/m1/s1;
InChI Key
OWVIRVJQDVCGQX-VSGBNLITSA-N;
Complexity
574
Covalently-Bonded Unit Count
1
Defined Atom Stereocenter Count
2
Exact Mass
466.214g/mol
H-Bond Acceptor
4
H-Bond Donor
2
Heavy Atom Count
35
Monoisotopic Mass
466.214g/mol
Rotatable Bond Count
6
Topological Polar Surface Area
58.9A^2
Application
(-)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane is a white to light yellow crystal powder serving as a versatile hydrogen-bonding organocatalyst. It plays a critical role in facilitating various chemical reactions by examining factors like acidity, deprotonation enthalpies, and hydrogen bonding. This catalyst is prominently utilized in the synthesis of cyclopropylamines through the addition reactions of Grignard reagents to amides. Furthermore, it is involved in enantioswitching for catalytic asymmetric hydroboration, creating derivative ligands for asymmetric hydroformylation of alkenes, and conducting amide-directed catalytic asymmetric hydroboration of trisubstituted alkenes. Additionally, it aids in the addition of deactivated alkyl Grignard reagents to aldehydes, highlighting its multifaceted applications in organic synthesis.
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