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

HRID 2166294Notes

Reaction equation

HRID 2166294 reaction equation
[C:1]1([CH2:7][O:8][C@H:9]2[C@H:15]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C@@H:14]([CH2:24][O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[O:13][C@@H:10]2[CH:11]=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.[C:35](=O)([O-])[O-:36].[K+].[K+].S(=O)(=O)(O)O>CO>[OH:12][CH2:11][C:10]1([O:13][C@H:14]([CH2:24][O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C@@H:15]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@@H:9]1[O:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:35][OH:36]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 108364862,5-anhydro-3,4,6-tris-O-(phenylmethyl)-D-mannose

Product 1

HCID 139625822,5-Anhydro-2-C-(hydroxymethyl)-3,4,6-tris-O-(phenylmethyl)-D-arabino-hexitol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1.18 g portion of 2,5-anhydro-3,4,6-tris-O-(phenylmethyl)-D-mannose prepared in accordance with Examples 1-3 was dissolved in 8.5 ml of methanol, treated with 5.11 ml of 37% formalin and 480 mg of potassium carbonate and the mixture immersed in an 85° C. bath. After 4 hours the mixture was cooled, neutralized with 3.5 ml of 10% sulfuric acid and the volatiles removed. The residue was extracted with chloroform, giving 0.86 g of the desired compound after chromatography.

Workup

  1. customimmersed in an 85° C.
  2. temperatureAfter 4 hours the mixture was cooled
  3. customthe volatiles removed
  4. extractionThe residue was extracted with chloroform

Sources & evidence

ORD record
ord-e14492d1b917417394036ecd0d4cf0ab
Source dataset
uspto-grants-1990_07
Patent number
US04943629

Reaction notes

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