Trityl chloride → HCID 11386706, compound

HRID 1461461Notes

Reaction equation

[CH2:1]([O:8][C@H:9]1[C@H:15]([OH:16])[C@@H:14]([CH2:17][OH:18])[O:13][CH:11]([OH:12])[C@@H:10]1[OH:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:21]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>N1C=CC=CC=1>[CH2:1]([O:8][C@H:9]1[C@H:15]([OH:16])[C@@H:14]([CH2:17][O:18][C:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[O:13][CH:11]([OH:12])[C@@H:10]1[OH:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3 (6 g)-and freshly purified chlorotriphenylmethane (5 g) in dry pyridine (50 mL) was heated for 2 hrs at 80° C. and then cooled to 0° C. 3-O-benzyl-6-O-triphenylmethyl-D-glucopyranose (16) could be isolated at this stage, or used further for acetylation. Acetic anhydride (15 mL)-was added, and the reaction mixture was heated at 80° C. until compound 16 had disappeared (TLC, ether:hexane, 1:2). The mixture was concentrated and a solution of the residue in chloroform (100 mL) was washed with aqueous potassium hydrogen sulfate and water, and concentrated. The crude 3-O-benzyl-6-O-triphenylmethyl-1,2,4-tri-O-acetyl-D-glucopyranose (17) was used in the next reaction. Small scale chromatography gave a material with 1H NMR data: 60:40 mixture of alpha:beta anomers 7.19-7.44 (m, 20 H, arom), 6.42 (d, 1 H, alpha-H)-, 5.67 (d, 1 H, beta-H), 3.07-5.23 (8 H), 2.17 (s, 3 H, Ac-alpha), 2.16 (s, 3H, Ac-beta) 2.01 (s, 3 H Ac-α, 1.99 (s, 3 H, Ac-beta), 1.69 (s, 3 H, Ac-β), 1.66 (s, 3 H, Ac-alpha).

Workup

temperaturecooled to 0° C

Sources & evidence

ORD record: ord-21952993b920454db2582d2e498fb7b5
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05075433

Reaction notes

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