ChemicalBook CAS DataBase List 2-Deoxy-alpha-D-erythropentofuranosyl chloride 3,5-bis(4-methylbenzoate)

2-Deoxy-alpha-D-erythropentofuranosyl chloride 3,5-bis(4-methylbenzoate) synthesis

7synthesis methods

Product Name:2-Deoxy-alpha-D-erythropentofuranosyl chloride 3,5-bis(4-methylbenzoate)
CAS Number:4330-21-6
Molecular formula:C21H21ClO5
Molecular Weight:388.84

78185-64-5 Synthesis

Methyl 2-deoxy-3,5-di-O-p-toluoyl-α-D-ribo-furanoside

78185-64-5
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2-Deoxy-alpha-D-erythropentofuranosyl chloride 3,5-bis(4-methylbenzoate)

4330-21-6
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$7.00/250mg

Yield:4330-21-6 58%

Reaction Conditions:

with hydrogenchloride;glacial acetic acid;acetyl chloride at 20; for 0.5 h;

Steps:

2.3 Synthesis of compound 4

To a solution of (2R,3S,5S)-5-methoxy-2-(((4- methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate (250 g, 0.65 mol, 1 eq) in acetic acid (393 mL) was added a freshly prepared solution of saturated HC1 in acetic acid (using acetyl chloride and acetic acid) (618 mL) slowly at room temperature. After completion of the addition, further acetyl chloride (50 mL) was added slowly at room temperature. The reaction mixture was stirred for a further 30 minutes, upon which time a colourless precipitate formed that was isolated by filtration to give (2R,3S,5R)-5-chloro-2- (((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate as a colourless solid (145 g, 58 %). LCMS: 407 ( 8.10 - 7.84 (m, 5H), 7.34 - 7.20 (m, 5H), 6.52 (d, J = 5.1 Hz, 1H), 5.61 (ddd, J = 7.4, 2.8, 1.1 Hz, 1H), 4.91 (q, J = 3.5 Hz, 1H), 4.75 - 4.61 (m, 2H), 2.92 (ddd, J = 15.0, 7.5, 5.2 Hz, 1H), 2.79 (dd, J = 15.2, 1.1 Hz, 1H), 2.47 (d, J - 4.8 Hz, 6H).

References:

WO2022/81739,2022,A1 Location in patent:Page/Page column 32-33