Sodium borohydride → HCID 18632082, compound

HRID 621757Notes

Reaction equation

HRID 621757 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@@H:8]1[C@@H:21]([O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)[C@H:20]([O:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][O:31]2)[C@@H:19]([CH2:36][O:37][CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][O:39]2)[O:18][C:9]1([OH:17])[CH2:10][P:11]([O:15][CH3:16])([O:13][CH3:14])=[O:12].[BH4-].[Na+]>C(OCC)C>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@H:8]([C@H:21]([C@@H:20]([C@@H:19]([CH2:36][O:37][CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][O:39]1)[OH:18])[O:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][O:31]1)[O:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1)[C@@H:9]([OH:17])[CH2:10][P:11]([O:13][CH3:14])([O:15][CH3:16])=[O:12]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 131715926HCID 131715926, compound

Product 1

HCID 18632082HCID 18632082, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3,4,5,7-tetra-O-(tetrahydropyranyl)-1-deoxy-1-(dimethoxyphosphoryl)-D-gluco-2-heptulopyranose (26.6 g) in diethyl ether (300 ml) was added sodium borohydride (3.0 g). The mixture was stirred overnight at room temperature. Insolubles were filtered off and washed with diethyl ether. The filtrate and the washings were combined, washed with 10%(W/V) sodium chloride solution, and dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The concentrate was chromatographed on a column of silica gel (1 l) with tolueneacetone (1:1). The eluate was concentrated under reduced pressure and dried under reduced pressure to give a mixture (18.8 g) of 3,4,5,7-tetra-O-(tetrahydropyranyl)-1-deoxy-1-(dimethoxyphosphoryl)-D-glycero-D-gulo-heptitol and 1,3,4,5-tetra-O-(tetrahydropyranyl)-7-deoxy-7-(dimethoxyphosphoryl-D-glycero-L-gulo-heptitol.

Workup

  1. filtrationInsolubles were filtered off
  2. washwashed with diethyl ether
  3. washwashed with 10%(W/V) sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationfollowed by concentration under reduced pressure
  6. customThe concentrate was chromatographed on a column of silica gel (1 l) with tolueneacetone (1:1)
  7. concentrationThe eluate was concentrated under reduced pressure
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-42618f5d18364c10be282b787dd57580
Source dataset
uspto-grants-1989_04
Patent number
US04824943

Reaction notes

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