Triethylamine → HCID 131723194, compound

HRID 843211Notes

Reaction equation

HRID 843211 reaction equation
[CH3:1][C@@H:2]([OH:12])[C@@H:3]([OH:11])[C@H:4]([O:9][CH3:10])[C@@H:5]([OH:8])[CH:6]=[O:7].[CH3:13][C@H:14]1[O:19][C@@H:18]([OH:20])[CH2:17][C@H:16]([O:21][CH3:22])[C@@H:15]1[OH:23].[Sn](Cl)Cl.C(N(CC)CC)C>ClCCl.FC(F)(F)S([O-])(=O)=O.[Ag+]>[CH3:1][C@@H:2]([OH:12])[C@@H:3]([OH:11])[C@H:4]([O:9][CH3:10])[C@@H:5]([OH:8])[CH:6]=[O:7].[CH3:13][C@H:14]1[O:19][C@@H:18]([OH:20])[CH2:17][C@H:16]([O:21][CH3:22])[C@@H:15]1[OH:23]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24479Stannous ChlorideHCID 1933946-Deoxy-3-O-methyl-D-glucoseHCID 4414172,6-Dideoxy-3-O-methylhexopyranose

Product 1

HCID 131723194HCID 131723194, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

A solution of thevetose (50 A) (1,5 g), cymarose (40) (1,3 g), and molecular sieves 4 Å in dichloromethane is stirred at room temperature for 1 hour. The reaction mixture is cooled to −15° C., and tin (II) chloride (0,8 g) and silver trifluoromethanesulphonate (1,1 g) are added. The mixture is stirred at −15° C. for 16 hours, after which triethylamine (0,5 ml) is added. The reaction product is filtered and the dichloromethane is evaporated. The dissaccharide (53) is purified by silica gel column chromatography eluting with ethyl acetate:hexane (2:8), yield 15%.

Workup

  1. filtrationThe reaction product is filtered
  2. customthe dichloromethane is evaporated
  3. customThe dissaccharide (53) is purified by silica gel column chromatography
  4. washeluting with ethyl acetate:hexane (2:8), yield 15%

Sources & evidence

ORD record
ord-60f0ea786d13431096096d5ab4ac2b4c
Source dataset
uspto-grants-2002_04
Patent number
US06376657B1

Reaction notes

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