365483
(Methoxycarbonylsulfamoyl)triethylammonium hydroxide, inner salt
97%
Synonym(s):
Burgess reagent, Methyl N-(triethylammoniosulfonyl)carbamate
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About This Item
Linear Formula:
CH3O2CNSO2N(C2H5)3
CAS Number:
Molecular Weight:
238.30
Beilstein:
1432131
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
97%
form
powder
mp
76-79 °C (lit.)
storage temp.
−20°C
SMILES string
CC[N+](CC)(CC)S(=O)(=O)[N-]C(=O)OC
InChI
1S/C8H18N2O4S/c1-5-10(6-2,7-3)15(12,13)9-8(11)14-4/h5-7H2,1-4H3
InChI key
YSHOWEKUVWPFNR-UHFFFAOYSA-N
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Application
Powerful dehydration agent for compounds such as secondary and tertiary alcohols, diols, amino alcohols, sugars, etc., including reactions with epoxides.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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K C Nicolaou et al.
Journal of the American Chemical Society, 126(20), 6234-6235 (2004-05-20)
Although glycosylamines constitute an important group of carbohydrates from the standpoint of biology and medicine, methods for their synthesis typically lack substrate generality and/or result in variable stereoselectivity, especially in complex contexts. In this communication, we report an operationally simple
Synlett, 9, 1247-1247 (2003)
A A Nagel et al.
Journal of medicinal chemistry, 25(7), 881-884 (1982-07-01)
Ring contraction of the neutral oleandrose sugar in the 14-membered-ring macrolide antibiotic oleandomycin (2) has been accomplished using [(methoxycarbonyl)sulfamoyl]triethylammonium hydroxide inner salt (1). The product of this interesting rearrangement, after methanolic hydrolysis of the 2'-acetate, is the 11-acetyl-3-O-(3"-methoxy-4"-vinylfuranosyl)oleandomycin (12). The
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