Allyl Alcohol → Allyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

HRID 1654626Notes

Reaction equation

[CH3:1][C:2]([O:4][CH2:5][CH:6]1[O:11][CH:10](Br)[CH:9]([O:13][C:14]([CH3:16])=[O:15])[CH:8]([O:17][C:18]([CH3:20])=[O:19])[CH:7]1[O:21][C:22]([CH3:24])=[O:23])=[O:3].[CH2:25]([OH:28])[CH:26]=[CH2:27]>>[C:14]([O:13][C@@H:9]1[C@@H:8]([O:17][C:18](=[O:19])[CH3:20])[C@@H:7]([O:21][C:22](=[O:23])[CH3:24])[C@@H:6]([CH2:5][O:4][C:2](=[O:3])[CH3:1])[O:11][C@H:10]1[O:28][CH2:25][CH:26]=[CH2:27])(=[O:15])[CH3:16]

Participants

Reactant 2

HCID 7858Allyl Alcohol

HCID 102932alpha-D-Galactopyranosyl bromide, tetraacetate

Product 1

HCID 7091156Allyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

Procedure

Acetobromogalactose (2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide) was mixed with allyl alcohol and mercuric cyanide via the Koenigs-Knorr glycosylation to obtain allyl β-D-galactopyranoside tetraacetate. This was followed by oxidation with 3-chloroperoxybenzoic acid in dichloromethane to obtain 2,3-epoxypropyl-β-D-galactopyranoside, 2,3,4,6-0-tetracetate.

Sources & evidence

ORD record: ord-f3fae10294f24df6b76a13678619336a
Source dataset: uspto-grants-1995_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05409902

Reaction notes

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