4-C-(Hydroxymethyl)-1,2-O-(1-methylethylidene)-3-O-(phenylmethyl)-α-D-erythro-pentofuranose
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4-C-(Hydroxymethyl)-1,2-O-(1-methylethylidene)-3-O-(phenylmethyl)-α-D-erythro-pentofuranose
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CAS No:
63593-03-3
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Formula:
C16H22O6
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Chemical Name:
4-C-(Hydroxymethyl)-1,2-O-(1-methylethylidene)-3-O-(phenylmethyl)-α-D-erythro-pentofuranose
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Synonyms:
α-D-erythro-Pentofuranose,4-C-(hydroxymethyl)-1,2-O-(1-methylethylidene)-3-O-(phenylmethyl)-;Furo[2,3-d]-1,3-dioxole,α-D-erythro-pentofuranose deriv.;4-C-(Hydroxymethyl)-1,2-O-(1-methylethylidene)-3-O-(phenylmethyl)-α-D-erythro-pentofuranose
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CAS No:
4-C-(Hydroxymethyl)-1,2-O-(1-methylethylidene)-3-O-(phenylmethyl)-α-D-erythro-pentofuranose Basic Attributes
310.346
310.34
1806241-263-5
4-C-(Hydroxymethyl)-1,2-O-(1-methylethylidene)-3-O-(phenylmethyl)-α-D-erythro-pentofuranose Use and Manufacturing
Into a 3000-mE round-bottom flask, was placed a solution of 269-4 (100 g, 359.32 mmol, 1.00 eq.) in tetrahydroffiran (500 mE) at RT. Water (500 mE) was added. To the mixture was added a NaOH solution (600 mE, 2 N in water) at 0° C. followed by aq. formaldehyde (240 mE, 37percent). The solution was stirred overnight at RT. The mixture was diluted with EA (1500 mE), washed with sat. NaC1 solution (3x500Into a 3000-mL round-bottom flask, was placed a solution of 278-4 (100 g, 359.32 mmol, 1.00 eq.) in tetrahydrofuran (500 mL) at RT. Water (500 mL) was added. To the mixture was added a NaOH solution (600 mL, 2 N in water) at 0° C. followed by aq. formaldehyde (240 mL, 37percent). The solution was stirred overnight at RT. The mixture was diluted with EA (1500 mL), washed with sat. NaCl solution (3×500 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by a silica gel column with EA:PE (1:1) to give 278-5 (52.5 g, 47percent) as a white solid. ESI MS m/z: 333 [M+Na]Into a 3000-mL round-bottom flask, was placed a solution of 266-4 (100 g, 359.32 mmol, 1.00 eq.) intetrahydrofuran (500 mL) at RT. Water (500 mL) was added. To the mixture was added a NaOH solution(600 mL, 2 N in water) at 0° C. followed by aq. formaldehyde (240 mL, 37percent). The solution was stirredovernight at RT. The mixture was diluted with EA (1500 mL), washed with sat. NaCl solution (3×500 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude productwas purified by a silica gel column with EA:PE (1:1) to give 266-5 (52.5 g, 47percent) as a white solid. ESI MSm/z: 333 [M+Na]+To 3-O-benzyl-1, 2-O-isopropylidene-α-D-ribo-pentodialdofuranose (68 g, 0.245 mol) in water (150 mL) and 1, 4-dioxane (170 mL) at 0 °C was added formaldehyde (135 mL of a 37percent aqueous solution) followed by sodium hydroxide (665 mL of a 1.0 M aqueous solution, 0.665 mol). The reaction mixture was stirred at room temperature for 6 d, then extracted with ethyl acetate (2 x 1 L). The combined organics were washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give 3-O-benzyl-4-(hydroxymethyl)-1, 2-O-isopropylidene-α-D-erythro-pentofuranose (77 g) as a yellow oil.
Computed Properties
Molecular Weight:310.34
XLogP3:0.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:5
Exact Mass:310.14163842
Monoisotopic Mass:310.14163842
Topological Polar Surface Area:77.4
Heavy Atom Count:22
Complexity:375
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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4-C-(Hydroxymethyl)-1,2-O-(1-methylethylidene)-3-O-(phenylmethyl)-α-D-erythro-pentofuranose
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