518379
Butylboronic acid N,N,N′,N′-tetramethyl-L-tartaric acid diamide ester
Synonym(s):
(4R,5R)-2-Butyl-N,N,N′,N′-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide
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About This Item
Empirical Formula (Hill Notation):
C12H23BN2O4
CAS Number:
Molecular Weight:
270.13
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352103
MDL number:
optical activity
[α]20/D -105°, c = 1.7% in chloroform
Quality Level
refractive index
n20/D 1.478 (lit.)
bp
178-179 °C (lit.)
density
1.072 g/mL at 25 °C (lit.)
functional group
amide
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
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
Preparation of biologically and pharmacologically active molecules
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
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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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 518379-5G | 04061832880143 |