Chloroform → 6-(5-Cholesten-3beta-yloxy)hexyl 6-amino-6-deoxy-1-thio-beta-D-galactopyranoside

HRID 1105877Notes

Reaction equation

HRID 1105877 reaction equation
C([O:4][C@@H:5]1[C@@H:45]([O:46]C(=O)C)[C@@H:44]([O:50]C(=O)C)[C@@H:43]([CH2:54][N:55]2C(=O)C3=CC=CC=C3C2=O)[O:42][C@H:6]1[S:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C@H:15]1[CH2:39][CH2:38][C@@:37]2([CH3:40])[C:17](=[CH:18][CH2:19][C@@H:20]3[C@@H:36]2[CH2:35][CH2:34][C@@:33]2([CH3:41])[C@H:21]3[CH2:22][CH2:23][C@@H:24]2[C@H:25]([CH3:32])[CH2:26][CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:16]1)(=O)C.C(Cl)(Cl)Cl.[NH4+].[OH-]>CO.C(N)CCC>[NH2:55][CH2:54][C@H:43]1[O:42][C@@H:6]([S:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C@H:15]2[CH2:39][CH2:38][C@@:37]3([CH3:40])[C:17](=[CH:18][CH2:19][C@@H:20]4[C@@H:36]3[CH2:35][CH2:34][C@@:33]3([CH3:41])[C@H:21]4[CH2:22][CH2:23][C@@H:24]3[C@H:25]([CH3:32])[CH2:26][CH2:27][CH2:28][CH:29]([CH3:30])[CH3:31])[CH2:16]2)[C@H:5]([OH:4])[C@@H:45]([OH:46])[C@H:44]1[OH:50]

Participants

6

Reactant 3

HCID 6212Chloroform2×HCID 14923Ammonium HydroxideHCID 1317125556-(5-Cholesten-3beta-yloxy)hexyl 2,3,4-tri-O-acetyl-6-deoxy-6-phthalimido-1-thio-beta-D-galactopyranoside

Product 1

HCID 1317125566-(5-Cholesten-3beta-yloxy)hexyl 6-amino-6-deoxy-1-thio-beta-D-galactopyranoside

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8007ButylamineSolvent

Procedure

A suspension of 6-(5-cholesten-3β-yloxy)hexyl 2,3,4-tri-O-acetyl-6-deoxy-6-phthalimido-1-thio-β-D-galactopyranoside (710 mg.) in methanol (10 ml.) and n-butylamine (10 ml.) is heated under reflux for 16 hours. The solution is evaporated to a crystalline mass. Chloroform is added and the solid is filtered and washed with chloroform. The combined filtrates are evaporated to a syrup which is put on a column of silica gel and eluted with chloroform-methanol-ammonium hydroxide (80:20:2). The desired fractions are combined and evaporated to a syrup which is triturated with ethyl ether to give crystals (390 mg. 76%); Rf 0.28 (CHCl3 --MeOH--NH4OH, 80:20:2), [α]D27 -29.5° C. (C 1.05, chloroform), m.s.: m/e 665 (M+ +1).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 16 hours
  3. customThe solution is evaporated to a crystalline mass
  4. additionChloroform is added
  5. filtrationthe solid is filtered
  6. washwashed with chloroform
  7. customThe combined filtrates are evaporated to a syrup which
  8. washeluted with chloroform-methanol-ammonium hydroxide (80:20:2)
  9. customevaporated to a syrup which
  10. customis triturated with ethyl ether
  11. customto give crystals (390 mg. 76%)

Sources & evidence

ORD record
ord-10253a64ac6b455bb910dc42648e08f9
Source dataset
uspto-grants-1982_01
Patent number
US04310505

Reaction notes

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