Sodium borohydride → HCID 15748195, compound

HRID 621756Notes

Reaction equation

HRID 621756 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:22]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:21]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C@@H:20]([CH2:39][O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[O:19][C:10]1([OH:18])[CH2:11][P:12]([O:16][CH3:17])([O:14][CH3:15])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>O1CCCC1>[CH2:1]([O:8][C@H:9]([C@H:22]([C@@H:21]([C@@H:20]([CH2:39][O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[OH:19])[O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C@@H:10]([OH:18])[CH2:11][P:12]([O:14][CH3:15])([O:16][CH3:17])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 14554062HCID 14554062, compound

Product 1

HCID 15748195HCID 15748195, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,4,5,7-tetra-O-benzyl-1-deoxy-1-(dimethoxyphosphoryl)-D-gluco-2-heptulopyranose (13.8 g) in tetrahydrofuran (140 ml) was added sodium borohydride (1.4 g). The mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and the residue was distributed between ethyl acetate (500 ml) and water (300 ml). The ethyl acetate layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was subjected to a silica gel column chromatography (550 ml) with tolueneacetone (2:1). The elute was concentrated under reduced pressure and dried under reduced pressure to give a mixture (12.4 g) of 3,4,5,7-tetra-O-benzyl-1-deoxy-1-(dimethoxyphosphoryl)-D-glycero-D-gulo-heptitol and 1,3,4,5-tetra-O-benzyl-7-deoxy-7-(dimethoxyphosphoryl)-D-glycero-L-gulo-heptitol.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. concentrationThe elute was concentrated under reduced pressure
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-56790760a7c54c55b897adcb8948181a
Source dataset
uspto-grants-1989_04
Patent number
US04824943

Reaction notes

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