Hydrochloric Acid → 2-Carboxyethyl 2,3,4-tri-O-acetyl-1-thio-beta-L-fucopyranoside

HRID 851677

Reaction equation

HRID 851677 reaction equation
[C:1]([O:4][C@H:5]1[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@H:9]([CH3:20])[O:8][C@@H:6]1[SH:7])(=[O:3])[CH3:2].I[CH2:22][CH2:23][C:24]([OH:26])=[O:25].C(N(CC)CC)C.Cl>ClCCl>[C:1]([O:4][C@H:5]1[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@H:9]([CH3:20])[O:8][C@@H:6]1[S:7][CH2:22][CH2:23][C:24]([OH:26])=[O:25])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 8856Propanoic acid, 3-iodo-HCID 232389082,3,4-tri-O-acetyl-1-thio-beta-L-fucopyranose

Product 1

HCID 228232862-Carboxyethyl 2,3,4-tri-O-acetyl-1-thio-beta-L-fucopyranosideYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranose (1.49 g, 4.87 mmol) and freshly crystallized 3-iodopropionic acid (0.97 g, 4.86 mmol) in dichloromethane (20 ml) containing triethylamine (1.35 ml) is kept for 16 hours at room temperature. Hydrochloric acid (2.5 N, 20 ml) and dichloromethane (10 ml) are added and the solution is washed with water, dried, and evaporated in vacuo to a residue that is put on a column of silica gel and eluted with chloroform-methanol-water, 92.5:7.5:0.75 (v/v/v). Compound 23 is isolated in 87% yield (1.6 g), and used, without further purification, for the preparation of 24.

Workup

  1. washthe solution is washed with water
  2. customdried
  3. customevaporated in vacuo to a residue that
  4. washeluted with chloroform-methanol-water, 92.5:7.5:0.75 (v/v/v)

Sources & evidence

ORD record
ord-112c947c294a458e9cd332d092afcaeb
Source dataset
uspto-grants-1983_05
Patent number
US04386026

Linked notes

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