beciparcil synthesis

7synthesis methods

Product Name:beciparcil
CAS Number:130782-54-6
Molecular formula:C12H13NO3S2
Molecular Weight:283.371

(2S,3R,4S,5S)-2-((4-cyanophenyl)thio)tetrahydro-2H-thiopyran-3,4,5-triyl triacetate

130782-78-4
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130782-54-6
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Yield:130782-54-6 89.7%

Reaction Conditions:

with sodium methylate in methanol;

Steps:

V Preparation of 4-cyanophenyl 1,5-dithio-β-D-xylopyranoside (Example 1)

PREPARATION V Preparation of 4-cyanophenyl 1,5-dithio-β-D-xylopyranoside (Example 1) Under a nitrogen atmosphere, 8.5 g (21.10^-3 mol) of 4-cyanophenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside (Example 1a) are suspended in 100 ml of methanol, and 2 ml of sodium methylate (8% w/v of Na in methanol) are then added. The reaction medium is stirred at room temperature until the starting material has completely dissolved (2 hours) and is then neutralized by the addition of Amberlite IR 120 H⁺ resin. The methanol is evaporated off under reduced pressure; the crude product obtained is recrystallized from an ethanol/water mixture (65/25 v/v) to give 5.3 g (yield: 89.7%) of the expected product. M.p.=175° C. [α]_D^20° C. =+35.8° (c=0.5; CH₃ OH)

References:

US5101048,1992,A