Water → HCID 70401471, compound

HRID 985968Notes

Reaction equation

HRID 985968 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].[OH2:32]>CC(O)C>[CH:2]1([N:31]([CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH3:13])[C:13](=[O:32])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[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]

Participants

5

Reactant 3

HCID 962WaterHCID 15793OctadecylamineHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 70401471HCID 70401471, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

90 g of D-glucose and 135 g of octadecylamine were heated at 50° C. in 1,000 ml of 2-propanol and 500 ml of water, with stirring, until a clear solution was formed. The solution was then left at room temperature overnight. The product was now filtered off with suction, washed with alcohol and ether, dried and, finally, recrystallized from ethanol/THF. 10 g of this N-octadecyl-β-D-glucopyranosylamine were suspended in 80 ml of THF and, after addition of 10 g of sodium carbonate, 7 g of oleoyl chloride in 10 ml of THF were added dropwise. After quantitative reaction (TLC in CH2Cl2 /CH3OH=13/1), the product was worked up as described in Example 12. Column purification with the eluting agent CH2Cl2 /CH3OH=13/1.

Workup

  1. customwas formed
  2. filtrationThe product was now filtered off with suction
  3. washwashed with alcohol and ether
  4. customdried
  5. customfinally, recrystallized from ethanol/THF
  6. additionafter addition of 10 g of sodium carbonate, 7 g of oleoyl chloride in 10 ml of THF
  7. additionwere added dropwise
  8. customAfter quantitative reaction (TLC in CH2Cl2 /CH3OH=13/1)
  9. customColumn purification with the eluting agent CH2Cl2 /CH3OH=13/1

Sources & evidence

ORD record
ord-5b844e3596b142c088c68f1f25414ff0
Source dataset
uspto-grants-1987_12
Patent number
US04710491

Reaction notes

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