Branched-chain sucroses: Synthesis and Wittig reaction of the 1′-aldehydo derivative of sucrose

1987 ◽  
Vol 162 (2) ◽  
pp. 209-215 ◽  
Author(s):  
Riaz Khan ◽  
Gita Patel
1970 ◽  
Vol 48 (20) ◽  
pp. 3253-3257 ◽  
Author(s):  
Alex Rosenthal ◽  
Matej Sprinzl

Oxidation of methyl 3,4-O-isopropylidene-β-D-arabinopyranoside (1) with ruthenium tetroxide afforded methyl 3,4-O-isopropylidene-β-D-erythro-pentopyranosid-2-ulose (2) in 78% yield. Condensation of methylenetriphenylphosphorane with 2 in the presence of H-butyllithium yielded methyl 3,4-O-isopropylidene-2-deoxy-2-C-methylene-β-D-erytho-pentopyranoside (3) in 55% yield. Reduction of the latter with 10% palladium-on-charcoal gave a 7:1 mixture of two isomeric 2-deoxy-2-C-methylpentoside derivatives in 95% yield: the preponderant product had the D-ribo configuration. The fully blocked methyl glycosides were de-isopropylidenated with methanolic hydrogen chloride to yield 6 and 7 and these were converted into the p-toluoyl esters (8) and (9). Attempts to utilize the latter in the synthesis of nucleosides of 2-deoxy-2-C-methyl pentoses were unsuccessful.


1969 ◽  
Vol 47 (23) ◽  
pp. 4473-4476 ◽  
Author(s):  
W. A. Szarek ◽  
J. S. Jewell ◽  
I. Szczerek ◽  
J. K. N. Jones

Addition of nitryl iodide to 3-deoxy-1,2:5,6-di-O-isopropylidene-3-methylene-α-D-ribo-hexofuranose (2), followed by treatment of the product with sodium borohydride, gave crystalline 3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-nitromethyl-α-D-allofuranose (3); the branched-chain unsaturated sugar (2) was prepared by way of a Wittig reaction with 1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose (1). Acid-catalyzed hydrolysis of 3 afforded 3-deoxy-3-C-nitromethyl-D-allose, which exists predominantly in the β-D-furanose form (4).


1968 ◽  
Vol 46 (17) ◽  
pp. 2868-2872 ◽  
Author(s):  
Alex Rosenthal ◽  
P. Catsoulacos

The Wittig reaction has been extended to yield a 2,3-dideoxy branched-chain sugar from 2-deoxy-3-ketose 3. Improvements in the procedures for the preparation of ketose (3) are also described.


1967 ◽  
Vol 8 (25) ◽  
pp. 2393-2396 ◽  
Author(s):  
Alex Rosenthal ◽  
L. (Benzing) Nguyen

2018 ◽  
Vol 88 (1-2) ◽  
pp. 80-89 ◽  
Author(s):  
Zahra Shakibay Novin ◽  
Saeed Ghavamzadeh ◽  
Alireza Mehdizadeh

Abstract. Branched chain amino acids (BCAA), with vitamin B6 have been reported to improve fat metabolism and muscle synthesis. We hypothesized that supplementation with BCAA and vitamin B6 would result in more weight loss and improve body composition and blood markers related to cardiovascular diseases. Our aim was to determine whether the mentioned supplementation would affect weight loss, body composition, and cardiovascular risk factors during weight loss intervention. To this end, we performed a placebo-controlled randomized clinical trial in 42 overweight and obese women (BMI = 25–34.9 kg/m2). Taking a four-week moderate deficit calorie diet (–500 kcal/day), participants were randomized to receive BCAA (6 g/day) with vitamin B6 (40 mg/day) or placebo. Body composition variables measured with the use of bioelectrical impedance analysis, homeostatic model assessment, and plasma insulin, Low density lipoprotein, High density lipoprotein, Total Cholesterol, Triglyceride, and fasting blood sugar were measured. The result indicated that, weight loss was not significantly affected by BCAA and vitamin B6 supplementation (–2.43 ± 1.02 kg) or placebo (–1.64 ± 1.48 kg). However, significant time × treatment interactions in waist to hip ratio (P = 0.005), left leg lean (P = 0.004) and right leg lean (P = 0.023) were observed. Overall, supplementation with BCAA and vitamin B6 could preserve legs lean and also attenuated waist to hip ratio.


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