ChemicalBook CAS DataBase List 2,3,4,6-TETRA-O-ACETYL-ALPHA-D-MANNOPYRANOSYL AZIDE

2,3,4,6-TETRA-O-ACETYL-ALPHA-D-MANNOPYRANOSYL AZIDE synthesis

7synthesis methods

Product Name:2,3,4,6-TETRA-O-ACETYL-ALPHA-D-MANNOPYRANOSYL AZIDE
CAS Number:53784-29-5
Molecular formula:C14H19N3O9
Molecular Weight:373.32

4163-65-9 Synthesis

1,2,3,4,6-PENTA-O-ACETYL-ALPHA-D-MANNOPYRANOSE

4163-65-9
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2,3,4,6-TETRA-O-ACETYL-ALPHA-D-MANNOPYRANOSYL AZIDE

53784-29-5
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Yield:53784-29-5 100%

Reaction Conditions:

with trimethylsilylazide;tin(IV) chloride in dichloromethane;Inert atmosphere;

Steps:

20 4.3 General procedure for glucopyranosyl azides (Procedure A)¹¹

General procedure: To a solution of the O-acetyl monosaccharide in dry CH₂Cl₂ (4mL/mmol), TMS-N₃ (2.5equiv) and SnCl₄ (0.5equiv) were added under nitrogen. The reaction was stirred until completion (TLC). The mixture was then diluted with CH₂Cl₂, and an equal volume of saturated NaHCO₃ solution was added and left for 30min under stirring. The mixture was then extracted with CH₂Cl₂, dried over anhydrous Na₂SO₄, and evaporated in vacuum. The product was purified by flash column chromatography. 4.20
2,3,4,6-Tetra-O-acetyl-α-d-mannopyranosyl azide 6
³⁰
To a solution of 1,2,3,4,6-penta-O-acetyl-α-d-mannopyranose (500 mg, 1.28 mmol) in 5 mL of dry CH₂Cl₂, TMS-N₃ (440 μL, 3.2 mmol) and SnCl₄ (115 μL, 0.64 mmol) were added following Procedure A.
The reaction product (480 mg, quant.) was used without purification. TLC R_f = 0.77 (n-hexane/EtOAc, 7:3); NMR data of this compound are consistent with those reported in Ref.
30
.