2,6-Anhydro-5-deoxy-D-arabino-hex-5-enitol triacetate → HCID 15699249, compound

HRID 653757Notes

Reaction equation

HRID 653757 reaction equation
[C:1]([O:4][C@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[O:8][CH:7]=[CH:6]1)(=[O:3])[CH3:2]>C(#N)C.C(O)CCC=C>[C:1]([O:4][C@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[O:8][C@H:7]([O:8][CH2:7][CH2:6][CH2:5][CH:10]=[CH2:9])[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 6401252,6-Anhydro-5-deoxy-D-arabino-hex-5-enitol triacetate

Product 1

HCID 15699249HCID 15699249, compoundYield 123.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 131814-Penten-1-OLSolvent

Procedure

A solution of 3,4,6-tri-O-acetyl-D-galactal (3.6 g) in acetonitrile (40 ml) anhydrous lithium bromide (4.7 g), 4-pentene-1-ol (4 ml), molecular sieves 4 Å (4 g) and the activated resin prepared as in Example 1 (5.1 g) was stirred at room temperature for 30 min. The product was isolated as described in Example 1 and purified on a column of Silica Gel using ethyl acetate-hexane (1:6) as eluant and yielded the title compound (2.92 g) and minor β-glycoside (0.32 g). [α]D20 (α-anomer)=+126°±2° (c 1.03, CHCl3); [α]D20 (β-anomer)=-9.4°±2° (c 1.03, CHCl3) 1H NMR δ (α anomer): 5.81 (m, --CH=C), 5.33 (d, H-1), 5.28 (m, H-3), 4.94-5.06 (m, H-4, C=CH 2), 4.16-4.06 (H-6a,b, H-5), 3.65 and 3.40 (m, O-CH2 -), 2.1 (m, H-2eq), 1.86 (m, H-2ax) MS (calc. mass for C17H26O8 =358.17). Obs. m/e 571.33, 357.21, 299.19, 273.05, 213.11.

Workup

  1. customThe product was isolated
  2. custompurified on a column of Silica Gel

Sources & evidence

ORD record
ord-4e256e5d9eeb40fa802157043b30499e
Source dataset
uspto-grants-1992_07
Patent number
US05128463

Reaction notes

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