methyl (1R,5R)-1,5-di-O-acetyl-1,5-dihydroxy-3-oxocyclohex-2-ene-1-carboxylate

Base Information

Chemical Name:methyl (1R,5R)-1,5-di-O-acetyl-1,5-dihydroxy-3-oxocyclohex-2-ene-1-carboxylate
CAS No.:286956-50-1
Molecular Formula:C₁₂H₁₄O₇
Molecular Weight:270.239
Hs Code.:

Synonyms:methyl (1R,5R)-1,5-di-O-acetyl-1,5-dihydroxy-3-oxocyclohex-2-ene-1-carboxylate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of methyl (1R,5R)-1,5-di-O-acetyl-1,5-dihydroxy-3-oxocyclohex-2-ene-1-carboxylate

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Technology Process of methyl (1R,5R)-1,5-di-O-acetyl-1,5-dihydroxy-3-oxocyclohex-2-ene-1-carboxylate

There total 4 articles about methyl (1R,5R)-1,5-di-O-acetyl-1,5-dihydroxy-3-oxocyclohex-2-ene-1-carboxylate 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: 83.0%

: 286956-49-8
methyl (1R,4R,5R)-1,5-di-O-acetyl-1,4,5-trihydroxycyclohex-2-ene-1-carboxylate

: 286956-50-1
methyl (1R,5R)-1,5-di-O-acetyl-1,5-dihydroxy-3-oxocyclohex-2-ene-1-carboxylate

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1002/(SICI)1099-0690(200005)2000:9<1745::AID-EJOC1745>3.0.CO;2-8

Reference yield:

: (3aR,5R,7R,7aS)-5,7-Diacetoxy-2-oxo-hexahydro-2λ⁴-benzo[1,3,2]dioxathiole-5-carboxylic acid methyl ester

: 286956-50-1
methyl (1R,5R)-1,5-di-O-acetyl-1,5-dihydroxy-3-oxocyclohex-2-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 0.91 g / NaIO₄ / RuCl₃*H₂O / ethyl acetate; acetonitrile / 1 h / 0 - 20 °C

2: DBU / tetrahydrofuran / 0.5 h / 70 °C

3: 1.35 g / aq. H₂SO₄ / tetrahydrofuran / 1 h / 20 °C

4: 83 percent / Dess-Martin perioninane / CH₂Cl₂ / 0.5 h / 20 °C

With sodium periodate; sulfuric acid; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; ruthenium trichloride; In tetrahydrofuran; dichloromethane; ethyl acetate; acetonitrile; 1: Oxidation / 2: Elimination / 3: Hydrolysis / 4: Oxidation;
DOI:10.1002/(SICI)1099-0690(200005)2000:9<1745::AID-EJOC1745>3.0.CO;2-8

Reference yield:

: (1R,4R,5R)-1,5-Diacetoxy-4-sulfooxy-cyclohex-2-enecarboxylic acid methyl ester

: 286956-50-1
methyl (1R,5R)-1,5-di-O-acetyl-1,5-dihydroxy-3-oxocyclohex-2-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 1.35 g / aq. H₂SO₄ / tetrahydrofuran / 1 h / 20 °C

2: 83 percent / Dess-Martin perioninane / CH₂Cl₂ / 0.5 h / 20 °C

With sulfuric acid; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 1: Hydrolysis / 2: Oxidation;
DOI:10.1002/(SICI)1099-0690(200005)2000:9<1745::AID-EJOC1745>3.0.CO;2-8