반응 #1160724

ord-a74209448369494f9e0dbd41b06c2355

반응 방정식

ClC(Cl)Cl
chloroform
[BH4-].[Na+]
Sodium borohydride
CC(=O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](OCCCCCCS[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]5O)CC[C@]4(C)[C@H]3CC[C@]12C
6-(pregn-5-en-20-one-3β-yloxy)hexyl 1-thio-β-D-mannopyranoside
CC(=O)O
acetic acid
→
CC(O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](OCCCCCCS[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]5O)CC[C@]4(C)[C@H]3CC[C@]12C
product
CC(O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](OCCCCCCS[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]5O)CC[C@]4(C)[C@H]3CC[C@]12C
6-(Pregn-5-en-20-ol-3β-yloxy)hexyl 1-thio-β-D-mannopyranoside

반응물

ClC(Cl)Cl
chloroform
[BH4-].[Na+]
Sodium borohydride
CC(=O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](OCCCCCCS[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]5O)CC[C@]4(C)[C@H]3CC[C@]12C
6-(pregn-5-en-20-one-3β-yloxy)hexyl 1-thio-β-D-mannopyranoside
CC(=O)O
acetic acid

시약

없음

용매

CCO
ethanol

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    온도the solution was cooled
  2. 2
    세척successively washed with water (3×), 1N sodium bicarbonate (2×), and water (1×)
  3. 3
    건조dried over anhydrous sodium sulfate
  4. 4
    기타The solvent was removed by rotoevaporation

실험 절차

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US04970199uspto-grants-1990_11