p-Toluenesulfonic acid → HCID 178503851, compound

HRID 967332Notes

Reaction equation

HRID 967332 reaction equation
[Si:1]([O:18][CH2:19][C@H:20]1[O:27][C@@H:24]([S:25][CH3:26])[C@H:23]([NH:28][C:29](=[C:31]2[C:36](=[O:37])[CH2:35][C:34]([CH3:39])([CH3:38])[CH2:33][C:32]2=[O:40])[CH3:30])[C@@H:22]([O:41][C:42](=[O:50])[C:43]2[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][CH:44]=2)[C@@H:21]1[OH:51])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:52]1[CH:57]=[CH:56][CH2:55][CH2:54][CH2:53]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>C(#N)C>[Si:1]([O:18][CH2:19][C@H:20]1[O:27][C@@H:24]([S:25][CH3:26])[C@H:23]([NH:28][C:29](=[C:31]2[C:32](=[O:40])[CH2:33][C:34]([CH3:39])([CH3:38])[CH2:35][C:36]2=[O:37])[CH3:30])[C@@H:22]([O:41][C:42](=[O:50])[C:43]2[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][CH:44]=2)[C@@H:21]1[O:51][CH:53]1[CH2:54][CH2:55][CH2:56][CH2:57][O:52]1)([C:14]([CH3:15])([CH3:17])[CH3:16])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 8471TriethylamineHCID 178503852HCID 178503852, compound

Product 1

HCID 178503851HCID 178503851, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl 6-O-(t-butyldiphenylsilyl)-3-O-(p-chlorobenzoyl)-2-deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethylamino]-1-thio-β- D-glucopyranoside (500 mg, 0.6 mmol), 3,4-dihydro-2H-pyran (5 mL) and -p-toluenesulphonic acid (5 mg) in dry acetonitrile (10 mL) was stirred at room temperature for 1 hour. The reaction mixture was adjusted to pH 7 with the addition of triethylamine and then evaporated to dryness. The residue was taken up in dichloromethane (30 mL), washed with water (2×10 mL) and the organic phase dried over MgSO4. The solvent was removed in vacuo and the residue was chromatographed using hexane—EtOA 2:1 as the mobile phase to give methyl 6-O-(t-butyldiphenylsilyl)-3-O-(p-chlorobenoyl)-2-deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethylamino]-4-O-tetrahydropyranyl-1-thio-β-D-glucopyranoside (5) (420 mg, 85%).

Workup

  1. customevaporated to dryness
  2. washwashed with water (2×10 mL)
  3. dry with materialthe organic phase dried over MgSO4
  4. customThe solvent was removed in vacuo
  5. customthe residue was chromatographed

Sources & evidence

ORD record
ord-c26b09ff37264660bdf20729b9ed601b
Source dataset
uspto-grants-2005_10
Patent number
US06953850B1

Reaction notes

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