(1R,2R,3S,4R,5S)-2-hydroxy-3,4,5-tri-O-(4-methoxybenzyl)-6-oxocyclohexyl acetate

Base Information

Chemical Name:(1R,2R,3S,4R,5S)-2-hydroxy-3,4,5-tri-O-(4-methoxybenzyl)-6-oxocyclohexyl acetate
CAS No.:137897-30-4
Molecular Formula:C₃₂H₃₆O₁₀
Molecular Weight:580.632
Hs Code.:

Synonyms:(1R,2R,3S,4R,5S)-2-hydroxy-3,4,5-tri-O-(4-methoxybenzyl)-6-oxocyclohexyl acetate

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Chemical Property of (1R,2R,3S,4R,5S)-2-hydroxy-3,4,5-tri-O-(4-methoxybenzyl)-6-oxocyclohexyl acetate

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Technology Process of (1R,2R,3S,4R,5S)-2-hydroxy-3,4,5-tri-O-(4-methoxybenzyl)-6-oxocyclohexyl acetate

There total 7 articles about (1R,2R,3S,4R,5S)-2-hydroxy-3,4,5-tri-O-(4-methoxybenzyl)-6-oxocyclohexyl acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 28.7%

: 137897-29-1
(Z)-methyl 6-O-acetyl-2,3,4-tri-O-methoxybenzyl-α-D-gluco-hex-5-enopyranoside

: 137897-30-4
(1R,2R,3S,4R,5S)-2-hydroxy-3,4,5-tri-O-(4-methoxybenzyl)-6-oxocyclohexyl acetate

Guidance literature:: palladium dichloride; In 1,4-dioxane; water; at 60 ℃; for 3h;
DOI:10.1021/jo001575h

Reference yield:

: 137915-48-1
methyl 2,3,4,-tri-O-(4-methoxybenzyl)-α-D-glucopyranoside

: 137897-30-4
(1R,2R,3S,4R,5S)-2-hydroxy-3,4,5-tri-O-(4-methoxybenzyl)-6-oxocyclohexyl acetate

Guidance literature:: Multi-step reaction with 3 steps

1: pyridine; trifluoroacetic acid; N,N-dicyclohexylcarbodiimide / benzene; dimethylsulfoxide / 24 h / 20 °C

2: 5.40 g / Et₃N; 4-(dimethylamino)pyridine / 1,2-dichloro-ethane / 3 h / Heating

3: 28.7 percent / PdCl₂ / H₂O; dioxane / 3 h / 60 °C

With pyridine; dmap; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium dichloride; In 1,4-dioxane; water; dimethyl sulfoxide; 1,2-dichloro-ethane; benzene; 3: Ferrier-II rearrangement;
DOI:10.1021/jo001575h

Reference yield:

: 137897-35-9
(2S,3S,4S,5R,6S)-6-Methoxy-3,4,5-tris-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde

: 137897-30-4
(1R,2R,3S,4R,5S)-2-hydroxy-3,4,5-tri-O-(4-methoxybenzyl)-6-oxocyclohexyl acetate

Guidance literature:: Multi-step reaction with 2 steps

1: 5.40 g / Et₃N; 4-(dimethylamino)pyridine / 1,2-dichloro-ethane / 3 h / Heating

2: 28.7 percent / PdCl₂ / H₂O; dioxane / 3 h / 60 °C

With dmap; triethylamine; palladium dichloride; In 1,4-dioxane; water; 1,2-dichloro-ethane; 2: Ferrier-II rearrangement;
DOI:10.1021/jo001575h