ChemicalBook CAS DataBase List L-GLUCOSE

L-GLUCOSE synthesis

4synthesis methods

Product Name:L-GLUCOSE
CAS Number:921-60-8
Molecular formula:C6H12O6
Molecular Weight:180.16

50-00-0 Synthesis

50-00-0
838 suppliers
$10.00/25g

50-99-7 Synthesis

50-99-7
969 suppliers
$6.00/25g

921-60-8
252 suppliers
$32.00/250mg

Yield:-

Reaction Conditions:

with L-proline;calcium hydroxide in methanol at 60; under 51.7162 - 103.432 Torr; for 0.45 h;Sealed tube;Industrial scale;

Steps:

3; 3A; 5

To a 250 mL round bottom flask equipped with a stir bar, Ca(OH)2 powder (0.1 g), L- Proline (0.1 g) and methanol (0.5 mL) was added to an aqueous formaldehyde solution (0.87 mol/L, 5.0 mL). The resulting suspension was heated at 60 °C using a hot oil bath while vigorously stirring. After 27 minutes, the milky white suspension turned yellow. The mixture was removed from the oil bath and quenched with an H2SO4 solution (1 mol/L, 1.5 mL). The solution was then filtered to give a light-yellow clear solution.75 pL of the light-yellow clear solution was diluted with water to 1.5 mL. The resulting solution was passed through an ion exchange resin pad to remove access proline. The samples are analyzed by HPLC (Shimadzu with Rezex ROA-Organic Acid H⁺(8%) column (300 mm*7.8mm) equipped with an ion exchange column for removing residual catalysts following literature procedures for HPLC analysis of sugars. The sugar standards (D- and L-glucose, galactose, fructose, ribose, and xylose, etc.) were purchased from Sigma Aldrich and used without further purification. The solid sugar products can be produced by removing solvent under reduced pressure.Further separation of D and L enantiomers can be done by (1) chiral resolution with SASP (reaction-crystallization-hydrolysis); or (2) chiral preparative HPLC or chiral capillary electrophoresis. Instead of chiral HPLC, optical rotation can also be used, which is measured using an Anton Paar MCP 200 system. A clear separation of glucose enantiomers was observed using CHIRALPAK AD-3 (250 x 4.6 mm i.d., 3 pm) (Fig. 5).

References:

WO2022/133033,2022,A1 Location in patent:Page/Page column 10-16