Pyridine → HCID 86634143, compound

HRID 1944839Notes

Reaction equation

HRID 1944839 reaction equation
[O:1]([CH2:11][CH:12]=[CH2:13])[CH:2]1[O:8][C@H:7]([CH2:9][OH:10])[C@@H:5]([OH:6])[C@H:3]1[OH:4].[C:14]1(C)[C:15]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:17]=[CH:18][CH:19]=1.N1C=CC=C[CH:26]=1>>[C:18]1([CH3:26])[CH:19]=[CH:14][C:15]([S:20]([O:10][CH2:9][C@H:7]2[O:8][CH:2]([O:1][CH2:11][CH:12]=[CH2:13])[C@H:3]([OH:4])[C@@H:5]2[OH:6])(=[O:21])=[O:22])=[CH:16][CH:17]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 8623o-Toluenesulfonyl chlorideHCID 11183107HCID 11183107, compound

Product 1

HCID 86634143HCID 86634143, compound

Procedure

A solution of allyl α,β-D-ribofuranoside 1 (18.6 g) in dry pyridine (100 mL) was cooled in an ice bath and p toluenesulfonyl chloride (22.4 g, 1.2 eq) was added portion-wise keeping the reaction temperature <5° C. The resulting solution was allowed to warm slowly to RT overnight and then was concentrated to dryness. 1,4-Dioxane (100 mL) was added to the residue and it was again concentrated to dryness. Chromatography of the residue afforded an anomeric mixture of the title compounds 3 as a syrup (17.6 g, 52%). 1H NMR (CDCl3) δ 7.80 (2H, d, J=8.3 Hz), 7.34 (2H, d, J=8.0 Hz), 5.85-5.72 (1H, m), 5.25-5.11 (2H, m), 4.94 (1H, s), 4.27-3.98 (6H, m), 3.87-3.80 (1H, m), 2.44 (3H, s); 13C NMR δ 145.5, 134.1, 133.0, 130.3, 128.4, 117.9, 106.6, 80.8, 75.2, 72.3, 71.0, 68.6, 22.0.

Workup

  1. customthe reaction temperature <5° C
  2. concentrationwas concentrated to dryness
  3. addition1,4-Dioxane (100 mL) was added to the residue and it
  4. concentrationwas again concentrated to dryness
  5. customChromatography of the residue afforded

Sources & evidence

ORD record
ord-32d7c3529c79416fa9ee6aaa5d90905e
Source dataset
uspto-grants-2013_03
Patent number
US08394950B2

Reaction notes

Loading…