Triethylamine → 6-(5-Cholesten-3beta-yloxy)hexyl 2,3,4-tri-O-acetyl-6-deoxy-6-phthalimido-1-thio-beta-D-galactopyranoside

HRID 1155300Notes

Reaction equation

HRID 1155300 reaction equation
C(N(CC)CC)C.[C:8]([O:11][C@@H:12]1[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@@H:17]([O:23][C:24](=[O:26])[CH3:25])[C@@H:16]([CH2:27][N:28]2[C:32](=[O:33])[C:31]3=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]3[C:29]2=[O:38])[O:15][C@H:13]1[SH:14])(=[O:10])[CH3:9].[CH3:39][CH:40]([CH2:42][CH2:43][CH2:44][C@H:45]([C@@H:47]1[C@:64]2([CH3:65])[C@H:50]([C@H:51]3[C@H:61]([CH2:62][CH2:63]2)[C@:59]2([CH3:60])[C:54]([CH2:55][C@@H:56]([O:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72]I)[CH2:57][CH2:58]2)=[CH:53][CH2:52]3)[CH2:49][CH2:48]1)[CH3:46])[CH3:41]>ClCCl>[C:8]([O:11][C@@H:12]1[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@@H:17]([O:23][C:24](=[O:26])[CH3:25])[C@@H:16]([CH2:27][N:28]2[C:32](=[O:33])[C:31]3=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]3[C:29]2=[O:38])[O:15][C@H:13]1[S:14][CH2:72][CH2:71][CH2:70][CH2:69][CH2:68][CH2:67][O:66][C@H:56]1[CH2:57][CH2:58][C@@:59]2([CH3:60])[C:54](=[CH:53][CH2:52][C@@H:51]3[C@@H:61]2[CH2:62][CH2:63][C@@:64]2([CH3:65])[C@H:50]3[CH2:49][CH2:48][C@@H:47]2[C@H:45]([CH3:46])[CH2:44][CH2:43][CH2:42][CH:40]([CH3:41])[CH3:39])[CH2:55]1)(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 128055222,3,4-Tri-O-acetyl-6-deoxy-6-phthalimido-1-thio-beta-D-galactopyranoseHCID 128055256-(5-Cholesten-3beta-yloxy)hexyl iodide

Product 1

HCID 1317125556-(5-Cholesten-3beta-yloxy)hexyl 2,3,4-tri-O-acetyl-6-deoxy-6-phthalimido-1-thio-beta-D-galactopyranosideYield 78.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.8 ml.) is added to a solution of 2,3,4-tri-O-acetyl-6-deoxy-6-phthalimido-1-thio-β-D-galactopyranose (2.5 g.) and 6-(5-cholesten-3β-yloxy)hexyl iodide (3.3 g.) in dichloromethane (20 ml.). The solution is kept at room temperature under nitrogen overnight, and washed with water, dried, and evaporated in vacuo to a syrup (4.71 g.). This material is put on a column of silica gel and eluted with chloroform followed by 2% ethyl acetate in chloroform. The desired fractions are combined and evaporated in vacuo to give the title compound (4.0 g., 78%); Rf 0.2 (CHCl3 -EtOAc. 95:5), [α]D27 -93° C. (C 1.18, chloroform); n.m.r. (chloroform-d); δ 7.60-7.91 (4 aromatic), 1.93, 2.03, and 2.24 (3 OAc) 0.68 (CH3 -18).

Workup

  1. washwashed with water
  2. customdried
  3. customevaporated in vacuo to a syrup (4.71 g.)
  4. washeluted with chloroform
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-7cb8033918014cd99e35e259fcefb0e9
Source dataset
uspto-grants-1981_11
Patent number
US04301152

Reaction notes

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