Sucrose → HCID 71752857, compound

HRID 374127Notes

Reaction equation

HRID 374127 reaction equation
[CH2:1]([OH:23])[C@H:2]1[O:7][C@H:6]([O:8][C@:9]2([CH2:18][OH:19])[O:13][C@H:12]([CH2:14][OH:15])[C@@H:11]([OH:16])[C@@H:10]2[OH:17])[C@H:5]([OH:20])[C@@H:4]([OH:21])[C@@H:3]1[OH:22].[C:24](Cl)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>N1C=CC=CC=1>[CH:28]1[CH:29]=[CH:30][C:25]([C:24]([O:23][CH2:1][C@H:2]2[O:7][CH:6]([O:8][C@:9]3([CH2:18][O:19][C:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[O:13][C@H:12]([CH2:14][O:15][C:24]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C@@H:11]([OH:16])[C@@H:10]3[OH:17])[C@H:5]([OH:20])[C@@H:4]([OH:21])[C@H:3]2[OH:22])([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 5988SucroseHCID 6456Trityl chloride

Product 1

HCID 71752857HCID 71752857, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

The procedure of Hough, Mufti, and Khan, Carbohydrate Res., Vol. 21, pp. 144-147 (1972), is modified as shown below. To a solution of 15 g of sucrose (43.82 mmol) in 225 ml of pyridine, a solution of 54.95 g of trityl chloride (197.1 mmol, 4.5 equiv.) in 50 ml of pyridine is added dropwise over a period of 30 minutes. The reaction mixture is then stirred at room temperature for 4 days. After 4 days, the solution is concentrated to a brown syrup, which is dissolved in methylene chloride. This solution is further washed successively with 1M hydrochloric acid, saturated sodium bicarbonate solution, water, and brine and then dried over anhydrous sodium sulfate. The methylene chloride solution it then concentrated in vacuo and the residue applied on a column of silica gel packed in methylene chloride:acetone (4:1) and eluted with that solvent. The 1',6,6'-tri-O-tritylsucrose is obtained (28.59 g) in 58.8% yield as an off-white solid with a melting point of 127° to 130° C.

Workup

  1. waitAfter 4 days
  2. concentrationthe solution is concentrated to a brown syrup, which
  3. dissolutionis dissolved in methylene chloride
  4. washThis solution is further washed successively with 1M hydrochloric acid, saturated sodium bicarbonate solution, water, and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe methylene chloride solution it then concentrated in vacuo
  7. washeluted with that solvent

Sources & evidence

ORD record
ord-785ec902297443fea2e26609658d9fa8
Source dataset
uspto-grants-1992_11
Patent number
US05166334

Reaction notes

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