594806

Sigma-Aldrich

Butylboronic acid N,N,N′,N′-tetramethyl-D-tartaric acid diamide ester

97%

Synonym(s):
(4S,5S)-2-Butyl-N,N,N′N′-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide
Empirical Formula (Hill Notation):
C12H23BN2O4
CAS Number:
Molecular Weight:
270.13
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

optical activity

[α]20/D +106°, c = 1% in chloroform

refractive index

n20/D 1.4780 (lit.)

bp

305-306 °C (lit.)

density

1.096 g/mL at 25 °C (lit.)

SMILES string

CCCCB1O[C@@H]([C@H](O1)C(=O)N(C)C)C(=O)N(C)C

InChI

1S/C12H23BN2O4/c1-6-7-8-13-18-9(11(16)14(2)3)10(19-13)12(17)15(4)5/h9-10H,6-8H2,1-5H3/t9-,10-/m0/s1

InChI key

AFQWQRBBIZKYTE-UWVGGRQHSA-N

Application

Butylboronic acid N,N,N′,N′-tetramethyl-D-tartaric acid diamide is a dioxaborolane ligand that can be used to prepare:
  • Enantioenriched spiropentanes via zinc catalyzed cyclopropanation of corresponding hydroxymethylallenes.
  • 1,2,3-trisubstituted cyclopropane derivatives by asymmetric cyclopropanation of allylic alcohols in the presence of zinc reagents.
  • Glycolipids plakosides A, B, and their derivatives by Sharpless asymmetric dihydroxylation and cyclopropanation reaction.

Packaging

1, 5 g in glass bottle

storage_class_code

10 - Combustible liquids

WGK Germany

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

> 110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Total synthesis and biological evaluation of glycolipids plakosides A, B and their analogs
Nicolaou KC, et al.
Helvetica Chimica Acta, 83(8), 1977-2006 (2000)
Enantioselective synthesis of spiropentanes from hydroxymethylallenes
Charette AB, et al.
Organic Letters, 3(21), 3293-3295 (2001)
Enantioselective synthesis of 1, 2, 3-trisubstituted cyclopropanes using gem-dizinc reagents
Zimmer LE and Charette AB
Journal of the American Chemical Society, 131(43), 15624-15626 (2009)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service