Ethyl 6-hydroxyhexanoate → 5-ethoxycarbonylpentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranoside

HRID 1732789Notes

Reaction equation

HRID 1732789 reaction equation
[C:1]([NH: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:23])[CH3:22])[O:7][C@@H:6]1Cl)(=[O:3])[CH3:2].[CH2:25]([O:27][C:28]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][OH:35])=[O:29])[CH3:26]>C(Cl)(Cl)Cl>[C:1]([NH: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:23])[CH3:22])[O:7][C@H:6]1[O:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][C:28]([O:27][CH2:25][CH3:26])=[O:29])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 357781Ethyl 6-hydroxyhexanoateHCID 111006222-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-glucopyranosyl chloride

Product 1

HCID 541910595-ethoxycarbonylpentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosideYield 74%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Condensation of 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride with 5-ethoxycarbonyl-1-pentanol under the same conditions as reported in example II gave a 74% yield of 5-ethoxycarbonylpentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside, mp 101°-102°, [α]D25 -16.8° (c 1.06, chloroform). De-O-acetylation of this compound using sodium methoxide gave after crystallization a 92% yield of 4 mp 154°-155° (melts and resolidifies) remelts 167°, [α]D18 -25.5° (c 1.1, water).

Sources & evidence

ORD record
ord-b160dca7daa64806ae3359f67fb8725d
Source dataset
uspto-grants-1980_12
Patent number
US04238473

Reaction notes

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