scholarly journals Selective Reduction of Carbohydrate Nitroolefins

1972 ◽  
Vol 50 (8) ◽  
pp. 1292-1295 ◽  
Author(s):  
Hans H. Baer ◽  
Werner Rank

Reduction of the four stereoisomeric methyl 4,6-O-benzylidene-2,3-dideoxy-3-nitro-hex-2-enopyranosides (1–4) with sodium borohydride gave in 80–90% yield the corresponding saturated nitro glycosides that possess an equatorial nitro group (5–8). Reduction of 1–4 with zinc and acetic acid gave in similar yields the corresponding 2,3-dideoxy-3-oximino glycosides (9–12). Two of the latter were deoximated to 2,3-dideoxy-3-oxo sugar derivatives.

2013 ◽  
Vol 464-465 ◽  
pp. 313-321 ◽  
Author(s):  
György Onyestyák ◽  
Szabolcs Harnos ◽  
Szilvia Klébert ◽  
Magdalena Štolcová ◽  
Alexander Kaszonyi ◽  
...  

1985 ◽  
Vol 14 (12) ◽  
pp. 1851-1854 ◽  
Author(s):  
Masashi Kijima ◽  
Yoko Nambu ◽  
Takeshi Endo

1982 ◽  
Vol 35 (4) ◽  
pp. 857
Author(s):  
J Collins ◽  
PS Cooper ◽  
RE Gall ◽  
A Georges

Monobromination of 5α-lanost-8-en-3-one (la) under kinetic conditions gave exclusively the 2β- bromo ketone (3a) whilst under equilibrium conditions the product contained 85% of the 2α-bromo ketone (2a). Monobromination of 5a-lanost-8-ene-3,7,11-trione (1b) under kinetic conditions gave the 2a-bromo ketone (2b); 33% of the 2β-bromo ketone (3b) was formed under equilibrium conditions. The configuration assigned to the bromo ketones (2b) and (3b) has been confirmed by reduction with sodium borohydride and treatment of the derived bromohydrins (4b) and (6b) with base to give the 2β,3β-epoxide (5b) and the 3-ketone (1b) respectively. Cleavage of the 2β,3β(-epoxide (5a) with acetic acid gave 2α-acetoxy-5α-lanost-8-en-3β-ol (7) as the major product and 3α-acetoxy-5α-lanost- 8-en-2β-ol (a), in a boat like conformation, as the minor product.


1973 ◽  
Vol 28 (11-12) ◽  
pp. 650-652
Author(s):  
Harold Rüdiger ◽  
Reinhard Siede

Abstract 5-Methyltetrahydrofolic acid is prepared from folic acid by sodium borohydride reduction, reac­ tion with formaldehyde and reduction to the methyl derivative by sodium borohydride. The crude product is precipitated as barium salt which after having been converted to the sodium salt by ion exchange is adsorbed to QAE-Sephadex and eluted by different acetic acid gradients in subsequent chromatographies. This method allows to process gram quantities on reasonably small columns


2006 ◽  
Vol 36 (6) ◽  
pp. 765-769 ◽  
Author(s):  
Francis X. Smith ◽  
Brian D. Williams ◽  
Eric Gelsleichter ◽  
Judy A. Podcasy ◽  
John T. Sisko ◽  
...  

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