Stereoselective synthesis of chirally deuterated (S)-D-(6- 2H1)glucose

Carbohydrate Research

Volumn 339, Issue 6, 2004, Pages 1173-1178

  Xu, Lin ^a   Price, Neil P J ^a,b  

^a UNIVERSITY OF ROCHESTER MEDICAL CENTER   (United States)

^b U S DEPARTMENT OF AGRICULTURE   (United States)

Author keywords

9 (6,6 Dimethylbicyclo 3.1.1 hept 2 yl)methyl 9 borabicyclo 3.3.1 nonane; Alpine Borane ; Chirally deuterated glucose; Mass spectrometry; NMR spectroscopy

Indexed keywords

ALCOHOLS; OXIDATION; REDUCTION; SYNTHESIS (CHEMICAL);

CHIRALLY DEUTERATED GLUCOSE; STEREOSELECTIVITY;

GLUCOSE;

9 [(6,6 DIMETHYLBICYCLO[3.1.1]HEPT 2 YL)METHYL] 9 BORABICYCLO[3.3.1]NONANE; ALCOHOL; ALDEHYDE; BORANE DERIVATIVE; GLUCOPYRANOSIDE; GLUCOSE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL MODIFICATION; DEPROTECTION REACTION; DEUTERON NUCLEAR MAGNETIC RESONANCE; MATERIALS; MOLECULAR MECHANICS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; STEREOCHEMISTRY; SWERN OXIDATION;

CARBOHYDRATE CONFORMATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEUTERIUM; GLUCOSE; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MODELS, CHEMICAL; NITROGEN; OXYGEN; STEREOISOMERISM;

EID: 1942421625     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2004.02.010     Document Type: Article

References (18)

1. Ohrui H., Nishida Y., Itoh H., Meguro H. J. Org. Chem. 56:1991;1726-1731.
2. Kakinuma K. J. Am. Chem. Soc. 103:1981;5614-5616.
3. Ohrui H., Nishida Y., Higuchi H., Hori H., Meguro H. Can. J. Chem. 65:1987;1145-1153.
4. Yamauchi N., Terachi T., Eguchi T., Kakinuma K. Tetrahedron. 50:1994;4125-4136.
5. Dong H., Mahmud T., Tornus I., Lee S., Floss H.G. J. Am. Chem. Soc. 123:2001;2733-2742.
6. Kakinuma K. Tetrahedron Lett. 50:1977;4413-4416.
7. Cornforth J.W., Redmond J.W., Eggerer H., Buckel W., Gutschow C. Nature. 221:1969;1212-1213.
8. Ohrui H., Horiki H., Kishi H., Meguro H. Agric. Biol. Chem. 47:1993;1101-1106.
9. Ohrui H., Nishida Y., Meguro H. Agric. Biol. Chem. 48:1984;1049-1053.
10. Ohrui H., Misawa T., Meguro H. Agric. Biol. Chem. 48:1984;1825-1829.
11. Falcone-Hindley M.L., Davis J.T. J. Org. Chem. 63:1998;5555-5561.
12. Brown H.C., Ramachandran P.V. J. Organomet. Chem. 500:1995;1-19.
13. Midland M.M., Greer S. Synthesis. 1978;845-846.
14. Midland M.M., Asirwatham G., Cheng J.C., Miller J.A., Morell L.A. J. Org. Chem. 59:1994;4438-4442.
15. Roseman S. J. Am. Chem. Soc. 74:1952;4467-4468.
16. Chida N., Yamada E., Ogawa S. J. Carbohydr. Chem. 17:1988;555-570.
17. Lipták A., Jodál I., Nánási P. Carbohydr. Res. 44:1975;1-11.
18. Singh S., Nambiar S., Porter R.A., Sander T.L., Taylor K.G., Doyle R.J. J. Org. Chem. 54:1989;2300-2307.