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Sigma-Aldrich

(Methoxycarbonylsulfamoyl)triethylammonium hydroxide, inner salt

97%

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Synonym(s):
Burgess reagent, Methyl N-(triethylammoniosulfonyl)carbamate
Linear Formula:
CH3O2CNSO2N(C2H5)3
CAS Number:
Molecular Weight:
238.30
Beilstein/REAXYS Number:
1432131
MDL number:
PubChem Substance ID:
NACRES:
NA.22

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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This Item
151653748773416444
Methyl hydrazinocarboxylate 97%

151653

Methyl hydrazinocarboxylate

Ethyl 1H-imidazole-1-carboxylate

748773

Ethyl 1H-imidazole-1-carboxylate

3-(Boc-amino)-1-propanol 97%

416444

3-(Boc-amino)-1-propanol

storage temp.

−20°C

storage temp.

-

storage temp.

2-8°C

storage temp.

-

mp

76-79 °C (lit.)

mp

70-73 °C (lit.)

mp

-

mp

-

form

powder

form

-

form

liquid

form

liquid

Application

Powerful dehydration agent for compounds such as secondary and tertiary alcohols, diols, amino alcohols, sugars, etc., including reactions with epoxides.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

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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