ChemicalBook CAS DataBase List D-(-)-Salicin

D-(-)-Salicin synthesis

5synthesis methods

Product Name:D-(-)-Salicin
CAS Number:138-52-3
Molecular formula:C13H18O7
Molecular Weight:286.28

2-[(Acetyloxy)methyl]phenyl β-D-glucopyranoside 2,3,4,6-tetraacetate

16643-37-1
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138-52-3
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Yield:138-52-3 80 mg

Reaction Conditions:

with sodium methylate in methanol at 20; for 1 h;Inert atmosphere;

Steps:

Glucosides 24-28 General procedure

General procedure: To a solution 2 and the acceptor ArOH (3.0 equiv) in dry DCM (0.1 M) was added afreshly prepared solution of BF3?OEt2 (1.0 equiv., 1M in dry DCM). The solution wasstirred 1 h and followed by TLC (30:70; EtOAc : hexanes). A solution of NaHCO3(aq) wasadded and the mixture was extracted with DCM, washed with brine, dried over Na2SO4,filtered and concentrated in vacuo. The α/β ratio was measured by 1H NMR on the crude.The residue was treated with a freshly prepared solution MeONa (0.25 equiv., 0.5 M inmethanol) in dry methanol (0.3 M). The solution was stirred at r.t. for 1 h andneutralized with Amberlite IR-120 H+, filtered and concentrated in vacuo to give a whitesolid. Quick flash column chromatography (10:90; MeOH:DCM) removed excess of ArOHand led to the β-D anomer, which was recrystallized in hot ethanol.

References:

St-Pierre, Gabrielle;Dafik, Laila;Klegraf, Ellen;Hanessian, Stephen [Synthesis,2016,vol. 48,# 20,p. 3575 - 3588] Location in patent:supporting information