Formaldehyde → 2,5-Anhydro-2-C-(hydroxymethyl)-3,4,6-tris-O-(phenylmethyl)-D-arabino-hexitol

HRID 1073457Notes

Reaction equation

C1([CH2:7][O:8][C@H]2[C@H](OCC3C=CC=CC=3)[C@@H](COCC3C=CC=CC=3)OC2O)C=CC=CC=1.[C:32]1([CH2:38][O:39][C@H:40]2[C@H:46]([O:47][CH2:48][C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[C@@H:45]([CH2:55][O:56][CH2:57][C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)[O:44][C@@H:41]2[CH:42]=[O:43])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C=O.C(=O)([O-])[O-].[K+].[K+].S(=O)(=O)(O)O>CO>[OH:43][CH2:42][C:41]1([O:44][C@H:45]([CH2:55][O:56][CH2:57][C:58]2[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=2)[C@@H:46]([O:47][CH2:48][C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[C@@H:40]1[O:39][CH2:38][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:7][OH:8]

Participants

Conditions

Temperature: 85 °C

Procedure

A 1 177 g portion of 2,5-anhydro-3,4,6-tris-O-(phenylmethyl)-D-mannose (prepared in accordance with Example 20) was dissolved in 8.5 ml of methanol and then treated with 5.11 ml of 37% formalin and 480 mg of potassium carbonate. This mixture was heated under argon at 85° C. for 4 hours, then cooled, neutralized with 10% sulfuric acid and evaporated. The residue was taken up in chloroform, washed with brine and evaporated. The residual oil was flash chromatographed, eluting with hexane:ethyl acetate (3:2). The combined fractions gave 860 mg of the desired product, [α]D26 =+37°±2 (c. 0.555, chloroform).

Workup

temperaturecooled
customevaporated
washwashed with brine
customevaporated
customchromatographed
washeluting with hexane:ethyl acetate (3:2)

Sources & evidence

ORD record: ord-40a40158e9b245d6808d220c85d4b06b
Source dataset: uspto-grants-1990_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04968790

Reaction notes

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