D-Mannopyranosyl bromide, tetraacetate → HCID 69736117, compound
Reaction equation
[C:1]([O:4][C@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=O)[CH3:22])[O:7][CH:6]1Br)(=[O:3])[CH3:2].C([CH:28]1[CH:33](O)[CH:32](O)[CH:31](O)[CH:30]([CH2:37]O)O1)C=C>>[C:30]1([CH:6]2[O:7][CH:8]([CH2:19][OH:20])[CH:9]([OH:15])[CH:10]([OH:11])[CH:5]2[OH:4])[CH:31]=[CH:32][CH:33]=[CH:28][CH:37]=1.[C:12]([O:11][CH:10]1[CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH:6]([C:31]2[CH:30]=[CH:37][CH:28]=[CH:33][CH:32]=2)[O:7][CH:8]([CH2:19][O:20][C:21]([C:22]2[CH:5]=[CH:10][CH:9]=[CH:8][CH:19]=2)([C:30]2[CH:31]=[CH:32][CH:33]=[CH:28][CH:37]=2)[C:31]2[CH:30]=[CH:37][CH:28]=[CH:33][CH:32]=2)[CH:9]1[O:15][C:16](=[O:18])[CH3:17])(=[O:14])[CH3:13]Participants
Procedure
6-Phenyl-2-hydroxymethyl-tetrahydro-pyran-3,4,5-triol was prepared from 2,3,4,6-tetra-O-acetyl-D-mannopyranosyl bromide according to the method of Hurd and Holysz (Hurd, C. D. and Holysz, R. P., (1950). Reactions of polyacylglycosyl halides with Grignard reagents. J. Am. Chem Soc., 1950, vol 72, 1732-1738) incorporated herein by reference. This compound (2.4 g, 10 mmol) was tritylated, acetylated in the same manner as described for to 2-allyl-6-hydroxymethyl-tetrahydropyran-3,4,5-triol in Example 3 to give acetic acid 4,5-diacetoxy-6-phenyl-2-trityloxymethyl-tetrahydro-pyran-3-yl ester (3.1 g, 64%). This compound was detritylated, phosphorylated and deacetylated as described for acetic acid 4,5-diacetoxy-6-allyl-2-trityloxymethyl-tetrahydropyran-3-yl ester in Example 3 above to give 6-phenyl-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl phosphoric acid ester (22% overall yield) ESMS (−ve) 319 (M−H).
Sources & evidence
- ORD record
- ord-f86f5b6d0fbc47dd87b2893878e6b2f1
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06878690B2
Reaction notes
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