ChemicalBook CAS DataBase List Methyl 3,5-di-O-benzyl-a-D-ribofuranoside

Methyl 3,5-di-O-benzyl-a-D-ribofuranoside synthesis

4synthesis methods

Product Name:Methyl 3,5-di-O-benzyl-a-D-ribofuranoside
CAS Number:80795-53-5
Molecular formula:C20H24O5
Molecular Weight:344.4016

64363-77-5 Synthesis

Methyl 2,3,5-tri-O-benzyl-D-ribofuranoside

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Methyl 3,5-di-O-benzyl-a-D-ribofuranoside

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Yield:80795-53-5 89.5%

Reaction Conditions:

with tin(IV) chloride in dichloromethane at -20 - 0; for 23.5 h;

Steps:

A-5.1

Step 1: To a solution of the compound from Step 2 of Example A-2 (111 g, 255.45 mmol) in CH₂Cl₂ (800 mL) at -20 °C was added dropwise a solution of stannic chloride (280.99 mL, IM solution in CH₂Cl₂, 280.99 mmol) over a period of 30 min while stirring and maintaining the temperature between -20 and -10 ⁰C. After the solution was kept at 0 °C for 23 h, the, reaction mixture was quenched carefully by the addition of saturated NaHCO₃ solution (1 L) over a 10-min period. Tin salts were removed via filtration through Celite, and from the filtrate the organic phase was separated. The aqueous layer was extracted with chloroform (1000 mL). The combined organic extracts were washed twice with water (500 mL) and brine (200 mL), and dried over MgSO₄. After filtration, the filtrate was concentrated to furnish crude product as dark yellow oil. The crude oil was purified by flash chromatography (silica gel 1 kg, eluting with ethyl acetate in hexanes) to furnish 78.7 g (89.5%) of 4-(benzyloxy)-5- (benzyloxymethyl)-2-methoxy-tetrahydrofuran-3-ol as an oil. ¹H NMR (DMSO-^): δ 7.35- 7.26 (m, 10H), 4.77 (d, J= 4.3 Hz, IH), 4.56 (dd, J= 42.8 and 12.4 Hz, 2H), 4.46 (bs, 2H), 4.06 (dd, J= 8.3 and 4.3 Hz, IH), 3.98 (dd, J= 6.6 and 4.7 Hz, IH), 3.68 (dd, J= 6.6 and 3.8 Hz, IH), 3.44 (d, J= 4.5 Hz, 2H), 3.30 (bs, 3H); IR (neat) 3554.8, 3030.7, 2926.0, 2912.0, 2863.2, 1957.1, 1732.1, 1650.4, 1494.8, 1452.4, 1414.7, 1362.0, 1323.2, 1269.2, 1187.7, 1124.5, 1095.7, 1040.0, 914.4, 853.3, 738.8 and 698.5 cm ^"1J MS (ES⁺) 367.38 (M+Na); Anal. Calcd for C₂₀H₂₄O₅: C, 69.74; H, 7.02. Found: C, 69.84; H, 7.00.

References:

WO2006/50161,2006,A2 Location in patent:Page/Page column 63

α-D-Ribofuranoside, methyl 2,3,5-tris-O-(phenylmethyl)-

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References

100-44-7 Synthesis

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References

52485-92-4 Synthesis

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References