70491-70-2

Basic information

• Product Name: D-GLUCOSE(6-13C)
• CAS NO: 70491-70-2
• Molecular Formula: C₆H₁₂O₆
• Molecular Weight: 0
• Mol File: 70491-70-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: D-GLUCOSE(6-13C)(CAS DataBase Reference)
• NIST Chemistry Reference: D-GLUCOSE(6-13C)(70491-70-2)
• EPA Substance Registry System: D-GLUCOSE(6-13C)(70491-70-2)

Safety Data

• Hazardous Substances Data: 70491-70-2(Hazardous Substances Data)

Upstream product

• 82913-29-9 (6-⁽¹³⁾C)cyanhydrin 
• 40010-63-7 C₈⁽¹³⁾CH₁₆O₆ 
• 40010-55-7 α- and β-D-<1-13C>mannose 

Downstream Products

• 90913-08-9 [4-13C]-D-erythrose 
• 1185549-51-2 C₂⁽¹³⁾CH₆O₄ 
• 1185549-49-8 C₃⁽¹³⁾CH₈O₅ 
• 144-62-7 oxalic acid 
• 81277-97-6 2-¹³C-glycolic acid 
• 87-69-4 L-Tartaric acid 
• 488-31-3 xylaric acid 
• 139657-60-6 C₄⁽¹³⁾CH₁₀O₅ 
• 1185549-38-5 C₄⁽¹³⁾CH₁₀O₆ 
• 1185549-17-0 C₅⁽¹³⁾CH₁₀O₆ 
• 1185548-92-8 C₅⁽¹³⁾CH₁₂O₇ 
• 1185549-01-2 C₅⁽¹³⁾CH₁₀O₇ 
• 1185549-10-3 C₅⁽¹³⁾CH₁₀O₇ 
• 215533-91-8 D-[6-13C]-glucaric acid 

Relevant articles and documents

Stable, isotopically substituted carbohydrates: an improved synthesis of (6-13C)aldohexoses.

1,2-O-Isopropylidene-alpha-D-xylo-pentodialdo-1,4-furanose (1) has been used as the parent aldose in the preparation of D-(6-13C)glucose and L-6-13C)idose via cyanohydrin reduction. The addition of K13CN (pH 6.8, 5 min) to 1 yields D-gluco and L-ido cyanohydrins that are readily reduced with H2 and Pd-BaSO4, to give 1,2-O-isopropylidene-alpha-D-gluco-hexodialdo-1,4-furanose (2; approximately 65%) and 1,2-O-isopropylidene-beta-L-ido-hexodialdo-1,4-furanose (3; 35%). Aldehydes 2 and 3 are reduced in situ with NaBH4, the resulting alcohols are deprotected with aqueous acid, and the aldoses are chromatographed on Dowex 50 X-8 (Ca2+) ion-exchange resin (200-400 mesh), to yield D-(6-13C)glucose (6) and L-(6-13C)idose (7). Molybdate epimerization of 6 and 7 yields D-(6-13C)mannose and L-(6-13C)gulose, respectively. A similar reaction scheme may be applied to methyl 2,3-O-isopropylidene-beta-D-ribo-pentodialdo-1,4-furanoside to generate the remaining four (6-13C)aldohexoses. This route is considerably simpler than the traditional Kiliani-Fischer route, and higher yields are obtained.

HYDROXIDE-CATALYZED ISOMERIZATION OF D-(1-13C)MANNOSE: EVIDENCE FOR THE INVOLVEMENT OF 3,4-ENEDIOLS

The KOH-catalyzed isomerization of D-(1-13C)mannose under anaerobic conditions was studied by 13C-n.m.r. spectroscopy.D-(1-13C)Glucose and D-(1-13C)fructose are generated during the reaction, as expected.In addition, however, (6-13C)glucose, (6-13C)mannose, and (6-13C)fructose are produced in small proportions, possibly via symmetrical 3,4-enediol intermediates.The involvement of the latter structures in 13C-label shifting is inferred from the observation of (1-13C)sorbose and (6-13C)sorbose in the reaction mixture.