Acetic Acid → HCID 131716484, compound

HRID 2166295Notes

Reaction equation

HRID 2166295 reaction equation
[C:1]1([CH2:7][O:8][CH2:9][C@:10]2([O:32][C@H:31]([CH2:33][O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C@@H:22]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@@H:13]2[O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.C(O)(=O)C.[PH:53](=[O:60])([O:57][CH2:58][CH3:59])[O:54][CH2:55][CH3:56]>CCOCC>[CH2:55]([O:54][P:53]([O:57][CH2:58][CH3:59])([CH:11]([OH:12])[C@:10]1([CH2:9][O:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[O:32][C@H:31]([CH2:33][O:34][CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C@@H:22]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C@@H:13]1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:60])[CH3:56]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 88609007HCID 88609007, compoundHCID 178476833HCID 178476833, compound

Product 1

HCID 131716484HCID 131716484, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 7.20 g portion of 2,5-anhydro-2-C-[(phenylmethoxy)methyl]-3,4,6-tris-O-(phenylmethyl)-D-glucose was dissolved in 6.7 ml of phosphonic acid, diethyl ester and treated with 620 μl of triethylamine under argon. After 4.5 hours 800 μl of acetic acid was added, the resulting yellow oil taken up in ether, washed with water, saturated with hexane, rewashed with water, then twice with brine, dried and evaporated. The residual oil was flash chromatographed, eluting 75 ml fractions with ether:toluene (2:1).

Workup

  1. washwashed with water, saturated with hexane
  2. dry with materialtwice with brine, dried
  3. customevaporated
  4. customchromatographed
  5. washeluting 75 ml fractions with ether:toluene (2:1)

Sources & evidence

ORD record
ord-075f9d7025454151803ba328de47fba2
Source dataset
uspto-grants-1990_07
Patent number
US04943629

Reaction notes

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