Sodium borohydride → HCID 59557726, compound

HRID 1175304Notes

Reaction equation

HRID 1175304 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:5]([CH2:54][C:55]2[CH:60]=[CH:59][C:58]([CH2:61][CH3:62])=[CH:57][CH:56]=2)=[CH:6][C:7]([C@H:15]2[C@H:20]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C@@H:19]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C@H:18]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C@@H:17]([CH2:45][O:46][CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[O:16]2)=[C:8]([CH:14]=1)[CH2:9][O:10][CH2:11][CH:12]=[O:13]>C1COCC1>[Cl:3][C:4]1[C:5]([CH2:54][C:55]2[CH:60]=[CH:59][C:58]([CH2:61][CH3:62])=[CH:57][CH:56]=2)=[CH:6][C:7]([C@H:15]2[C@H:20]([O:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C@@H:19]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C@H:18]([O:37][CH2:38][C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[C@@H:17]([CH2:45][O:46][CH2:47][C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=3)[O:16]2)=[C:8]([CH:14]=1)[CH2:9][O:10][CH2:11][CH2:12][OH:13]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59557725HCID 59557725, compound

Product 1

HCID 59557726HCID 59557726, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaBH4 (13 mg, 0.34 mmol) was added into a solution of 2-(5-chloro-4-(4-ethylbenzyl)-2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzyloxy)acetaldehyde (intermediate O-2) (140 mg, 0.17 mmol) in THF (10 mL) and stirred for 1.5 h. The reaction mixture was quenched by MeOH (2 mL), then evaporated to dryness. The residue was purified by preparative TLC, which afforded 2-(5-chloro-4-(4-ethylbenzyl)-2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzyloxy)ethanol (intermediate O-3) (135 mg, 0.169 mmol, yield 96.2%).

Workup

  1. customThe reaction mixture was quenched by MeOH (2 mL)
  2. customevaporated to dryness
  3. customThe residue was purified by preparative TLC, which

Sources & evidence

ORD record
ord-3ae9a9abada94c1c8762db01464b510a
Source dataset
uspto-grants-2010_11
Patent number
US07838498B2

Reaction notes

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