Acetyl chloride → 2-(hydroxymethyl)-6-phenylmethoxyoxane-3,4,5-triol

HRID 475664Notes

Reaction equation

[O:1]=[CH:2][C@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[C:13](Cl)(=O)[CH3:14]>C(O)C1C=CC=CC=1>[CH:5]1[CH:7]=[CH:9][C:13]([CH2:14][O:1][CH:2]2[O:10][CH:9]([CH2:11][OH:12])[CH:7]([OH:8])[CH:5]([OH:6])[CH:3]2[OH:4])=[CH:2][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

D-Mannose (30 g, 167 mmol) and acetyl chloride (13 mL, 167 mmol) was dissolved in benzyl alcohol (250 mL) and heated to 50° C. for 1 h. The resulting solution was concentrated by low pressure distillation. The resulting residue was purified by flash column chromatography (ethyl acetate/methanol, 9:1) and recrystallised from isopropanol/petrol to afford the title compound (29.34 g, 70%) as a white crystalline solid m.p. 126-127° C. [Lit 128-129° C.]; [α]D26+102.0 (c, 1.1 in MeOH); [Lit. [α]D18+73.1 (c, 1.4 in H2O)]; δH (400 MHz, CD3OD) 3.62 (1H, ddd, J4,5 9.5 Hz, J5,6 2.3 Hz, J5,6′ 5.5 Hz, H-5), 3.68 (1H, at, J9.3 Hz, H-4), 3.73-3.78 (2H, m, H-3, H-6), 3.85-3.88 (2H, m, H-2, H-6′), 4.75, 4.52 (2H, ABq, J11.6 Hz, CH2), 4.86 (1H, d, J1,2 1.8 Hz, H-1), 7.28-7.38 (5H, m, ArH).

Workup

concentrationThe resulting solution was concentrated by low pressure distillation
customThe resulting residue was purified by flash column chromatography (ethyl acetate/methanol, 9:1)
customrecrystallised from isopropanol/petrol

Sources & evidence

ORD record: ord-0c8b0db450774348ba484a27941c5e68
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637578B2

Reaction notes

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