Diisopropylamine → Methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-beta-D-galactopyranoside

HRID 1683154Notes

Reaction equation

HRID 1683154 reaction equation
C(O[C@@H:5]1[O:18][C@H:17]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[C@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@H:7]([O:8][C:9](=[O:11])[CH3:10])[C@H:6]1[N:24]1[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]2[C:25]1=[O:34])(=O)C.[CH3:35][S:36][Si](C)(C)C.C(NC(C)C)(C)C>C(Cl)Cl>[C:9]([O:8][C@H:7]1[C@@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@@H:17]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:18][C@@H:5]([S:36][CH3:35])[C@@H:6]1[N:24]1[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]2[C:25]1=[O:34])(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 77513Silane, trimethyl(methylthio)-HCID 127757051,3,4,6-Tetra-o-acetyl-2-deoxy-2-phthalimido-beta-d-galactopyranose

Product 1

HCID 11059664Methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-beta-D-galactopyranosideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-galactose (680 mg, 1.425 mmol), methylthiotrimethylsilane (0.8 ml, 5.64 mmol), and trimethyl silyl triflate (0.32 ml, 1.66 mmol) in CH2Cl2 was stirred at room temperature for 2 days. Diisopropylamine (~1 ml) was added, diluted with CH2Cl2 (~50 ml) and washed with saturated NaHCO3 solution and water, respectively. The organic layer was dried (Na2SO4) and evaporated to dryness. Column chromatography (heptane-EtOAc) gave pure 20 (630 mg, 95%) as an amorphous powder, having [α]D24 +25° (c1, CHCl3).

Workup

  1. washwashed with saturated NaHCO3 solution and water
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-c79eb21ada994dbe9e45b36319b4d72e
Source dataset
uspto-grants-1997_06
Patent number
US05637569

Reaction notes

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