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S7556

Sigma-Aldrich

Sulfur trioxide pyridine complex

97%

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Synonym(s):
NSC 75831, Pyridine sulfur trioxide complex
Empirical Formula (Hill Notation):
C5H5NO3S
CAS Number:
Molecular Weight:
159.16
Beilstein/REAXYS Number:
3704116
EC Number:
MDL number:
UNSPSC Code:
12352303
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

reaction suitability

reagent type: oxidant

SMILES string

O=S(=O)=O.c1ccncc1

InChI

1S/C5H5N.O3S/c1-2-4-6-5-3-1;1-4(2)3/h1-5H;

InChI key

UDYFLDICVHJSOY-UHFFFAOYSA-N

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Application

  • Sulfation agent

Reactant for:
  • Preparation of azido anologs of pregnanolone
  • Sulfate esters of morphine derivatives
  • Gold nanoparticles capped with sulfate-ended ligands as anti-HIV agents
Sulfur trioxide-pyridine (SO3-py) complex can be used to convert the allylic or benzylic hydroxyl group of compounds such as geraniol, farnesol, and 1-indanol into sulfate monoester, which is a good leaving group. This method is highly useful in the total synthesis of sesquiterpenes.
As a sulfating agent, SO3-py complex can be used for the preparation of sulfated-chitins, sulfated hyaluronan (HyaS) derivatives and sulfated starch.

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A method for deoxygenation of allylic and benzylic alcohols.
Corey E J and Achiwa K
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