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
UNSPSC Code:
12352108
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1432131
Assay:
97%
Form:
powder
InChI
1S/C8H18N2O4S/c1-5-10(6-2,7-3)15(12,13)9-8(11)14-4/h5-7H2,1-4H3
SMILES string
CC[N+](CC)(CC)S(=O)(=O)[N-]C(=O)OC
InChI key
YSHOWEKUVWPFNR-UHFFFAOYSA-N
assay
97%
form
powder
mp
76-79 °C (lit.)
functional group
amine
storage temp.
−20°C
Quality Level
Application
Powerful dehydration agent for compounds such as secondary and tertiary alcohols, diols, amino alcohols, sugars, etc., including reactions with epoxides.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Synlett, 9, 1247-1247 (2003)
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
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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