Benzyl Alcohol → HCID 69980896, compound

HRID 966397Notes

Reaction equation

HRID 966397 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si](OS(C(F)(F)F)(=O)=O)(CC)(CC)CC.ClC(Cl)(Cl)C(=N)O[C@H:28]1[O:49][C@H:48]([CH2:50][O:51][CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[C@@H:39]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C@H:34]([O:35][CH2:36][CH:37]=[CH2:38])[C@H:29]1[O:30][C:31](=[O:33])[CH3:32].C(N(CC)CC)C>ClCCl>[C:31]([O:30][C@@H:29]1[C@@H:34]([O:35][CH2:36][CH:37]=[CH2:38])[C@H:39]([O:40][CH2:41][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C@@H:48]([CH2:50][O:51][CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[O:49][C@H:28]1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:33])[CH3:32]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 2733308Triethylsilyl trifluoromethanesulphonateHCID 69350255HCID 69350255, compound

Product 1

HCID 69980896HCID 69980896, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.62 mL (3 eq.) of benzyl alcohol and 130 μL (0.1 eq.) of TESOTf are added to 3.07 g (1 eq.) of 2-O-acetyl-3-O-allyl-4,6-di-O-benzyl-α-D-gluco-pyranosyl trichloroacetimidate (M=586.5) in 25 mL of dichloromethane at 0° C. in the presence of 2.5 g of 4 Å molecular seives. After 1 hour of reaction at 0° C., the medium is neutralised with triethylamine, filtered and concentrated. Purification over silica gel [flash; eluent: toluene/ethyl acetate (98/2; v/v)] enables isolating 2.52 g of benzyl 2-O-acetyl-3-O-allyl-4,6-di-O-benzyl-β-D-glucopyranoside (M=532).

Workup

  1. customAfter 1 hour of reaction at 0° C.
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customPurification over silica gel [flash; eluent: toluene/ethyl acetate (98/2; v/v)]

Sources & evidence

ORD record
ord-c38cde88e21a4a459d19713b19472f88
Source dataset
uspto-grants-2005_10
Patent number
US06951934B2

Reaction notes

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