(4S,5R)-5-hydroxy-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester

Base Information

Chemical Name:(4S,5R)-5-hydroxy-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester
CAS No.:185810-87-1
Molecular Formula:C₉H₁₂O₅
Molecular Weight:200.191
Hs Code.:

Synonyms:(4S,5R)-5-hydroxy-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester

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Chemical Property of (4S,5R)-5-hydroxy-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester

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Technology Process of (4S,5R)-5-hydroxy-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester

There total 11 articles about (4S,5R)-5-hydroxy-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester 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: 90.0%

: 185810-86-0
(1R,4S,5R)-1,4-dimethoxy-6-oxabicyclo[3.2.1]octane-3,7-dione

: 185810-87-1
(4S,5R)-5-hydroxy-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester

Guidance literature:: With potassium hydrogencarbonate; In methanol; for 12h; Ambient temperature;
DOI:10.1021/jo961713w

Reference yield: 85.0%

: 950897-46-8
(3R,4S,5R)-3,5-dihydroxy-4-methoxycyclohex-1-ene-1-carboxylic acid methyl ester

: 185810-87-1
(4S,5R)-5-hydroxy-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester

Guidance literature:: With dipyridinium dichromate; In N,N-dimethyl-formamide; at 15 ℃; for 2h;
DOI:10.1002/hlca.200790138

Reference yield:

: 77-95-2
D-(-)-quinic acid

: 185810-87-1
(4S,5R)-5-hydroxy-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: p-TsOH*H₂O / dimethylformamide; benzene / 12 h / Heating

2: 1.) Bu₂SnO / 1.) DMF, benzene, reflux, 4h, 2.) DMF, benzene, reflux, 6 h

3: 90 percent / KH / tetrahydrofuran / 1.) room temperature, 1 h, 2.) reflux, 1 h

4: 98 percent / H₂ / Pd(OH)2/C / methanol / Ambient temperature

5: 90 percent / NaIO₄, RuO₂*xH₂O / ethyl acetate; H₂O; acetone / 16 h / Ambient temperature

6: 90 percent / KHCO₃ / methanol / 12 h / Ambient temperature

With ruthenium(IV) oxide; sodium periodate; hydrogen; potassium hydride; di(n-butyl)tin oxide; potassium hydrogencarbonate; toluene-4-sulfonic acid; palladium dihydroxide; In tetrahydrofuran; methanol; water; ethyl acetate; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1021/jo961713w