Acetic Acid → 6-(Pregn-5-en-20-ol-3beta-yloxy)hexyl 1-thio-alpha-D-mannopyranoside

HRID 2051531Notes

Reaction equation

HRID 2051531 reaction equation
[BH4-].[Na+].[S:3]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C@H:22]1[CH2:41][CH2:40][C@@:39]2([CH3:42])[C:24](=[CH:25][CH2:26][C@@H:27]3[C@@H:38]2[CH2:37][CH2:36][C@@:35]2([CH3:43])[C@H:28]3[CH2:29][CH2:30][C@@H:31]2[C:32](=[O:34])[CH3:33])[CH2:23]1)[C@@H:4]1[O:12][C@H:11]([CH2:13][OH:14])[C@@H:9]([OH:10])[C@H:7]([OH:8])[C@@H:5]1[OH:6].C(O)(=O)C.C(Cl)(Cl)Cl>C(O)C>[S:3]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C@H:22]1[CH2:41][CH2:40][C@@:39]2([CH3:42])[C:24](=[CH:25][CH2:26][C@@H:27]3[C@@H:38]2[CH2:37][CH2:36][C@@:35]2([CH3:43])[C@H:28]3[CH2:29][CH2:30][C@@H:31]2[CH:32]([OH:34])[CH3:33])[CH2:23]1)[C@H:4]1[O:12][C@H:11]([CH2:13][OH:14])[C@@H:9]([OH:10])[C@H:7]([OH:8])[C@@H:5]1[OH:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6212ChloroformHCID 4311764Sodium borohydrideHCID 867413636-(pregn-5-en-20-one-3beta-yloxy)hexyl 1-thio-beta-D-mannopyranoside

Product 1

HCID 1317168996-(Pregn-5-en-20-ol-3beta-yloxy)hexyl 1-thio-alpha-D-mannopyranoside

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (60 mg) was added to a solution of 6-(pregn-5-en-20-one-3β-yloxy)hexyl 1-thio-β-D-mannopyranoside (250 mg) in absolute ethanol (7 ml). After stirring at room temperature for 4 hours, the solution was cooled and glacial acetic acid (10 ml) was slowly added. The solution was added to chloroform (100 ml) and successively washed with water (3 ×), 1N sodium bicarbonate (2 ×), and water (1 ×) and dried over anhydrous sodium sulfate. The solvent was removed by rotoevaporation to give the product as a fine white solid. The 200 MHz NMR spectrum of the peracetylated derivative was in accord with the desired structure. TLC data and Rf values are given in the above Table.

Workup

  1. temperaturethe solution was cooled
  2. washsuccessively washed with water (3 ×), 1N sodium bicarbonate (2 ×), and water (1 ×)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed by rotoevaporation

Sources & evidence

ORD record
ord-d3610b63fcd242e9bcb2a132a4a1b6af
Source dataset
uspto-grants-1991_05
Patent number
US05019568

Reaction notes

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