ChemicalBook CAS DataBase List 1,6-ANHYDRO-BETA-D-GLUCOPYRANOSE

1,6-ANHYDRO-BETA-D-GLUCOPYRANOSE synthesis

8synthesis methods

Product Name:1,6-ANHYDRO-BETA-D-GLUCOPYRANOSE
CAS Number:498-07-7
Molecular formula:C6H10O5
Molecular Weight:162.14

β-D-Glucopyranose, 1,6-anhydro-3-O-(phenylmethyl)-

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498-07-7
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Yield:498-07-7 170 g

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in methanol;ethyl acetate at 50; under 3800.26 Torr; for 4 h;

Steps:

1 Preparation of Phenyl-6-O-acetyl-2,3,4-tri-O-benzoyl-1-thio-α-L-idopyranoside
Modified and Optimized Procedure
l,6-anhydro-3-O-benzyl- -L-idopyranose (150g, 0.6 mol) was dissolved in the mixture EtOAc/MeOH (1 : 1, 1200 ml) and hydrogenated over 10% Pd/C (15 g) at 50 °C, 5 atm for 4h. The mixture was cooled to 20 °C, filtered through Celite and evaporated under reduced pressure. The oily residue and DMAP (22 g, 0.18 mol) were dissolved in CH₂C1₂ (400 ml) and Pyridine (404 ml, 5.0 mol) and the resulted mixture was cooled to 0 °C. Benzoyl chloride (276 g, 229 ml, 1.96 mol) was slowly added and the reaction was stirred for 3h at 20 °C (TLC monitoring). The volatiles were evaporated under reduced pressure and the solid residue was portioned between EtOAc (2L) and water (2L). The phases were separated, the organic one was washed with cold 2N aqueous HC1 (700 ml), water (500ml) and 10% aqueous NaHC0₃ (500 ml), dried over Na₂S0₄, filtered and concentrated under reduced pressure to give ~300g of solid residue. The residue was crystallized from Isopropanol afforded 265g (94%) yield) of the desired tribenzoate as white solid.

References:

OPKO PHARMACEUTICALS, LLC;AHMED, Tahir;GUTMAN, Arie;FEDOTEV, Irina;RUKHMAN, Igor;GROSSMAN, Olga WO2018/35050, 2018, A1 Location in patent:Paragraph 0073

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