2-Deoxy-β-D-arabino-hexopyranose tetraacetate synthesis

7synthesis methods

Product Name:2-Deoxy-β-D-arabino-hexopyranose tetraacetate
CAS Number:16750-07-5
Molecular formula:C14H20O9
Molecular Weight:332.3

13242-53-0 Synthesis

2,3,4,6-TETRA-O-ACETYL-ALPHA-D-MANNOPYRANOSYL BROMIDE

13242-53-0
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13121-61-4 Synthesis

2,3,4,6-Tetra-O-acetyl-1,5-anhydro-D-mannitol

13121-61-4
14 suppliers
$28.60/25MG

2-Deoxy-β-D-arabino-hexopyranose tetraacetate

16750-07-5
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Yield:13121-61-4 70% ，16750-07-5 7%

Reaction Conditions:

with sodium cyanoborohydride in tert-butyl alcohol; for 0.666667 h;UV-irradiation;Inert atmosphere;

Steps:

4.2. Typical procedure for light-promoted reduction²⁵

General procedure: (Conditions i): a t-BuOH solution (8 mL) containing 1 (200 mg, 0.486 mmol) and 95% NaBH₃CN (60.3 mg, 1 mmol) (see Table 1 for specific details and additives) was introduced in a quartz tube (～94 mL volume; 27 mm diameter) mounted at a close distance (～1 cm) of a medium-pressure mercury lamp (Hanovia, 450 W) inserted in a quartz jacket cooled down with tap-water and equipped with a filter (Vycor, Corex, Pyrex, see caption, Table 1). The tube was equipped with a magnetic stirring bar and argon was bubbled through the solution for at least 30 min prior irradiation. After completion of the reaction as indicated by TLC monitoring, or when judged appropriate, the solution was concentrated and the residue was dissolved in 30 mL CH₂Cl₂. After aqueous workup, drying of the organic phase over MgSO₄, and concentration under reduced pressure, the residue was resolved by silica gel column chromatography. Compounds of identical mobilities led to mixtures that were examined by ¹H NMR to estimate the product distribution. Similar assays with PhSH 10 mol % added were carried out (conditions ii). Reduction of compounds 14a-d was achieved similarly, using a quartz tube (13 mm diameter) equipped with a stirring bar. Compounds 14a-d (50 mg) and 95% NaBH₃CN (2 equiv) were dissolved in a 2:1 t-BuOH/CH₃CN mixture (6 mL) that was poured in the tube (argon atmosphere) prior to UV-light irradiation (Vycor filter).

References:

Bruyère, Isabelle;Tóth, Zoltan;Benyahia, Hamida;Xue, Jia Lu;Praly, Jean-Pierre [Tetrahedron,2013,vol. 69,# 46,p. 9656 - 9662] Location in patent:supporting information