Sodium hydride → (2S,3R,4R,5S,6R)-2-(Acetoxymethyl)-6-(((Z)-1-(4-chlorophenyl)-3-ethoxy-3-oxoprop-1-en-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Participants

Role	Name	HCID	Charge
Reactant	Sodium hydride	HCID 24758	—
Reactant	Ethyl 3-(4-chlorophenyl)-2-oxopropanoate	HCID 2736395	—
Reactant	(2S,3S,4R,5S,6R)-2-(Acetoxymethyl)-6-(((Z)-3-ethoxy-1-(2-fluorophenyl)-3-oxoprop-1-en-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate	HCID 66980300	—
Reactant	2,3,4,6 tetra-O-acetyl-alpha-D-galactose bromide	HCID 86702363	—
Product	(2S,3R,4R,5S,6R)-2-(Acetoxymethyl)-6-(((Z)-1-(4-chlorophenyl)-3-ethoxy-3-oxoprop-1-en-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate	HCID 66980310	66%

Reaction Steps

This was prepared as described for C4 using ethyl 3-(4-chlorophenyl)-2-oxopropanoate B7 (100 mg, 0.441 mmol), sodium hydride (11.65 mg, 0.485 mmol) and 2,3,4,6-tetra-O-acetyl-α-D-galactose bromide (181 mg, 0.441 mmol). The resulting compound was isolated in the form of white solid in 66% yield.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09221860B2
Source dataset	uspto-grants-2015_12
ORD ID	ord-8f112338261f4984990b8a33ea4a31f1
Source note	uspto-grants-2015_12