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365483

Sigma-Aldrich

(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:
29684-56-8
Molecular Weight:
238.30
Beilstein:
1432131
MDL number:
MFCD00077815
UNSPSC Code:
12352108
PubChem Substance ID:
24862529
NACRES:
NA.22

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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

Certificates of Analysis (COA)

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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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