ChemicalBook CAS DataBase List Spermidine

Spermidine synthesis

8synthesis methods

Product Name:Spermidine
CAS Number:124-20-9
Molecular formula:C7H19N3
Molecular Weight:145.25

The linker resin 2 was used in the synthesis of spermidine. In order to initiate the preparation the 2-nitrossulfonamide was anchored on the resin 2 by reaction in THF under reflux. The resulting resin 3 then reacted with 4-bromobutylphthalimide in acetonitrile in the presence of Cs2CO3 as base, generating the resin 4. Protected spermidine 5 was cleaved from resin 4 after treatment with hydrate hydrazine at room temperature. Spermidine 5 was previously prepared by our group in solution system utilizing Fukuyama's sulfonamide.

Synthesis and Characterization of a Linker for Primary Amines used in the Solid Phase Organic Synthesis of Spermidine
J. Braz. Chem. Soc., Vol. 22, No. 1, 86-91, 2011
DOI: 10.1590/S0103-50532011000100011

Carbamic acid, N-[4-[(3-aminopropyl)amino]butyl]-, 1,1-dimethylethyl ester

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124-20-9
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Yield:124-20-9 79.5%

Reaction Conditions:

with hydrogenchloride in methanol; for 4 h;Cooling with ice;

Steps:

1.S3; 2.S3; 3.S3; 4.S3; 5.S3

dissolving the compound d (0.3 mol) in the previous step in 450 mL of methanol, adding hydrochloric acid (250 mL, 3 mol) dropwise to an ice-water bath, stirring for 4 h, removing methanol under reduced pressure, and adjusting with 40% aqueous sodium hydroxide solution to pH=12, de-dried under reduced pressure, add 300 mL of tetrahydrofuran for extraction, filter, concentrate the filtrate to dryness, further rectify under reduced pressure, collect fractions at 124-126 °C under 12 mmHg vacuum to obtain compound e, namely spermidine 34.6 g, yield 79.5%, gas phase purity 99.5%.

References:

CN113735716,2021,A Location in patent:Paragraph 0032-0037