(3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)oxan-2-one → HCID 11330356, compound

HRID 1372194Notes

Reaction equation

HRID 1372194 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@@H:13]([CH2:32][O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:12][C:10]1=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li][CH3:42]>C1COCC1>[CH2:1]([O:8][C@@H:9]1[C@@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:14]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C@@H:13]([CH2:32][O:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[O:12][C:10]1([OH:11])[CH3:42])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10907626(3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)oxan-2-oneHCID 178418348HCID 178418348, compound

Product 1

HCID 11330356HCID 11330356, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

18 g (33 mmol) of 21a was dissolved in 200 mL of anhydrous THF under nitrogen. Cooled to −78° C. 45 mL of MeLi (1.6 M, 72 mmol) was added by a syringe. After 1 hour at −78° C., the reaction was quenched by a solution of 7 g of NH4Cl in 200 mL of H2O. TLC showed no starting material left, while a new spot corresponding to the product appeared. The mixture was extracted by 3×150 mL of ethyl acetate, washed by brine, dried over Na2SO4. After evaporation, a thick pale yellow oil was obtained which was turned into a white solid (17.6 g, 95% yield) with a melting point of 92–93° C. 300 MHz 1H NMR(CDCl3) δ: 1.41 (s, 3H, CH3); 2.58 (s, 1H, OH); 3.35–3.38 (d, 1H); 3.65–3.72 (m, 3H); 3.93–3.99 (m, 2H); 4.50–4.95 (m, 8H, 4-CH2), 7.14–7.36 (m, 20H). 13C NMR (CDCl3) δ: 26.59, 68.81, 71.55, 73.42, 74.85, 75.58, 75.68, 78.42, 83.18, 83.63, 97.36, 127.58, 127.65, 127.74, 127.82, 127.84, 127.91, 128.28, 128.32, 128.36, 128.41, 137.87, 138.21, 138.25, 138.64.

Workup

  1. customthe reaction was quenched by a solution of 7 g of NH4Cl in 200 mL of H2O
  2. waitleft, while a new spot corresponding to the product
  3. extractionThe mixture was extracted by 3×150 mL of ethyl acetate
  4. washwashed by brine
  5. dry with materialdried over Na2SO4
  6. customAfter evaporation
  7. customa thick pale yellow oil was obtained which

Sources & evidence

ORD record
ord-bc086621461346c39415f527703d954f
Source dataset
uspto-grants-2007_01
Patent number
US07157510B2

Reaction notes

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