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

HRID 1372193Notes

Reaction equation

HRID 1372193 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][CH:10]1[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(=O)C)(=O)C.O>CS(C)=O>[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=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 109405022,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranose

Product 1

HCID 10907626(3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)oxan-2-oneYield 94%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

27 g of 2,3,4,6-tetra-O-benzyl-D-glucopyranose (50 mmol) was dissolved in 153 mL of DMSO to form a clear solution. 102 mL of acetic anhydride was added dropwise. The resultant clear solution was allowed to stir at room temperature overnight. After 17 hours, GC-MS showed the lactone was gone and a new compound was observed. The yellow solution was poured into 600 mL of water and sat in a separation funnel overnight. The precipitated oil was passed through a silica gel column, eluted first with cyclohexane then gradually increasing polarity by adding acetone until the final eluent was cyclohexane: acetone=2:1. The appropriate portions were collected and evaporated to give a pale syrup. 25.2 g, yield: 94%. IR (v cm−1) 2867,1752.

Workup

  1. customto form a clear solution
  2. waitAfter 17 hours
  3. waitsat in a separation funnel overnight
  4. washeluted first with cyclohexane
  5. temperaturethen gradually increasing polarity
  6. additionby adding acetone until the final eluent
  7. customThe appropriate portions were collected
  8. customevaporated
  9. customto give a pale syrup

Sources & evidence

ORD record
ord-f020f389592a4c7cbd699f9d62999afe
Source dataset
uspto-grants-2007_01
Patent number
US07157510B2

Reaction notes

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