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

HRID 1155302Notes

Reaction equation

HRID 1155302 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[NH2:16][CH2:17][C@H:18]1[O:58][C@@H:22]([S:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][C@H:31]2[CH2:55][CH2:54][C@@:53]3([CH3:56])[C:33](=[CH:34][CH2:35][C@@H:36]4[C@@H:52]3[CH2:51][CH2:50][C@@:49]3([CH3:57])[C@H:37]4[CH2:38][CH2:39][C@@H:40]3[C@H:41]([CH3:48])[CH2:42][CH2:43][CH2:44][CH:45]([CH3:47])[CH3:46])[CH2:32]2)[C@H:21]([OH:59])[C@@H:20]([OH:60])[C@H:19]1[OH:61].[C:62](O)(=[O:80])[CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69]/[CH:70]=[CH:71]\[CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH3:79]>C(Cl)(Cl)Cl>[C:62]([NH:16][CH2:17][C@H:18]1[O:58][C@@H:22]([S:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][C@H:31]2[CH2:55][CH2:54][C@@:53]3([CH3:56])[C:33](=[CH:34][CH2:35][C@@H:36]4[C@@H:52]3[CH2:51][CH2:50][C@@:49]3([CH3:57])[C@H:37]4[CH2:38][CH2:39][C@@H:40]3[C@H:41]([CH3:48])[CH2:42][CH2:43][CH2:44][CH:45]([CH3:46])[CH3:47])[CH2:32]2)[C@H:21]([OH:59])[C@@H:20]([OH:60])[C@H:19]1[OH:61])(=[O:80])[CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69]/[CH:70]=[CH:71]\[CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH3:79]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 445639Oleic AcidHCID 1317125566-(5-Cholesten-3beta-yloxy)hexyl 6-amino-6-deoxy-1-thio-beta-D-galactopyranoside

Product 1

HCID 1317125576-(5-Cholesten-3beta-yloxy)hexyl 6-deoxy-6-oleamido-1-thio-beta-D-galactopyranosideYield 55.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of dicyclohexylcarbodiimide (106 mg.) in chloroform (5 ml.) is added to a solution of 6-(5-cholesten-3β-yloxy)hexyl 6-amino-6-deoxy-1-thio-β-D-galactopyranoside (309 mg.) and oleic acid (131.5 mg.) in chloroform (20 ml.). After 3 hours at room temperature, the reaction mixture is filtered and washed with water (20 ml.) and methanol (25 ml.). The organic layer is dried and evaporated in vacuo to a syrup which is crystallized from methanol to give the title compound (238 mg., 55%); m.p. 160°-163° C., [α]D27 -5.0° C. (C 1.0, chloroform).

Workup

  1. filtrationthe reaction mixture is filtered
  2. washwashed with water (20 ml.) and methanol (25 ml.)
  3. customThe organic layer is dried
  4. customevaporated in vacuo to a syrup which
  5. customis crystallized from methanol

Sources & evidence

ORD record
ord-7166584f3ca447f9b24f6129b092d386
Source dataset
uspto-grants-1981_11
Patent number
US04301152

Reaction notes

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