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Isopropanol → N-Hexadecyl-D-Glucosylamine

HRID 362766
Notes
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Reaction equation

HRID 362766 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].CC(O)C.[CH2:17]([NH2:33])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>O>[CH2:17]([NH:33][CH: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])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 8926HexadecylamineHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 21307606N-Hexadecyl-D-Glucosylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 2 L two neck round bottom flask equipped with condenser was charged with D(+) glucose (60 g, 0.333 moles), 2-propanol (900 mL), hexadecylamine (81 g, 0.334 moles) and deionized water (300 mL). The reaction was stirred and heated to 50°-55° celsius for 1 hour to obtain a homogeneous solution. The reaction was then allowed to run overnight at room temperature. The reaction precipitated out after 2-3 hours.

Workup

  1. temperatureheated to 50°-55° celsius for 1 hour
  2. customto obtain a homogeneous solution
  3. customThe reaction precipitated out after 2-3 hours

Sources & evidence

ORD record
ord-9d748b3db2ba4ce78f89bec119af9018
Source dataset
uspto-grants-1999_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05872111

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes