Octadecylamine → HCID 13361750, compound

HRID 482668Notes

Reaction equation

O=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[CH2:13]([NH2:31])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>>[CH2:13]([NH:31][C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

Reactant 2

HCID 15793Octadecylamine

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 13361750HCID 13361750, compound

Procedure

In the first process stage, glucose (a) is reacted with octadecylamine (b) to give N-octadecyl-β-D-glucopyranosylamine (c), which is acylated in the second process stage with oleyl chloride to give N-octadecyl-N-oleyl-β-D-glucopyranosylamine (d). In the third process stage, O-acylation is then carried out in position 6 by means of dodecanoyl chloride, and N-octadecyl-N-oleyl-(6-lauroyl-β-D-glucopyranosyl)-amide (I) is obtained.

Sources & evidence

ORD record: ord-00a5c8ba21b745d39d6db184ed9de449
Source dataset: uspto-grants-1986_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04574122

Reaction notes

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