(3S,4R,5R,6S)-3,4,5-Tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol → Dibenzyl 2,3,4-tri-O-benzyl-beta-L-fucopyranosyl phosphate

HRID 1491951Notes

Reaction equation

HRID 1491951 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]([CH3:32])[O:12][CH:10]1[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[P:33]([O-])([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34]>ClCCl>[P:33]([O:11][C@H:10]1[O:12][C@@H:13]([CH3:32])[C@@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@@H:15]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@@H:9]1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:34]

Participants

4

Reactant 2

HCID 2734155(3S,4R,5R,6S)-3,4,5-Tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-olHCID 4193600Dibenzylphosphate

Product 1

HCID 14216870Dibenzyl 2,3,4-tri-O-benzyl-beta-L-fucopyranosyl phosphateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,3,4-tri-O-benzyl-L-fucopyranose (0.50 g, 0.86 mmol) in 20 ml of dry dichloromethane and freshly recrystallized dibenzyl phosphate (0.24 g, 0.86 mmol) is stirred under a nitrogen atmosphere at room temperature for about 1 h. The solution is then concentrated and purified by chromatography (toluene/acetone 7:1). Dibenzyl 2,3,4-tri-O-benzyl-β-L-fucopyranosyl phosphate (5) is obtained in a yield of 95% as a colorless oil (0.57 g). TLC (toluene/acetone 7:1 gives an Rf of 0.45, [α]578 =-9.7 (c=1, chloroform).

Workup

  1. concentrationThe solution is then concentrated
  2. custompurified by chromatography (toluene/acetone 7:1)

Sources & evidence

ORD record
ord-8387b582bec7474cbc0e756c7b716400
Source dataset
uspto-grants-1994_12
Patent number
US05371203

Reaction notes

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