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518379

Sigma-Aldrich

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

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Synonym(s):
(4R,5R)-2-Butyl-N,N,N′,N′-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide
Empirical Formula (Hill Notation):
C12H23BN2O4
CAS Number:
161344-85-0
Molecular Weight:
270.13
MDL number:
MFCD04113606
UNSPSC Code:
12352103
PubChem Substance ID:
24874017
NACRES:
NA.22

optical activity

[α]20/D -105°, c = 1.7% in chloroform

Quality Level

100

refractive index

n20/D 1.478 (lit.)

bp

178-179 °C (lit.)

density

1.072 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-/m1/s1

InChI key

AFQWQRBBIZKYTE-NXEZZACHSA-N

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Application

Butylboronic acid N,N,N′,N′-tetramethyl-L-tartaric acid diamide ester can be used as a cyclopropanation ligand in one of the key steps for the total synthesis of:
  • (+)-Frondosin, a natural product from marine sponges.
  • Marine cyanobacterium natural products: coibacins A and B.

Reactant for:
Preparation of biologically and pharmacologically active molecules

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Coibacins A and B: Total synthesis and stereochemical revision
Carneiro VMT, et al.
The Journal of Organic Chemistry, 79(2), 630-642 (2014)
Total synthesis of (+)-frondosin A. Application of the Ru-catalyzed [5+ 2] cycloaddition.
Trost, Barry M and Hu, Yimin and Horne, Daniel B
Journal of the American Chemical Society, 129(38), 11781-11790 (2007)

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