[1R,2S,1(1S)]-1[D₁]-cis-1,2-Cyclohexanedimethyl bis(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate)

Base Information

• Chemical Name: [1R,2S,1(1S)]-1[D₁]-cis-1,2-Cyclohexanedimethyl bis(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate)
• CAS No.: 235779-97-2
• Molecular Formula: C₂₄H₄₂N₂O₆
• Molecular Weight: 455.599

Synonyms:[1R,2S,1(1S)]-1[D₁]-cis-1,2-Cyclohexanedimethyl bis(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate)

Chemical Property of [1R,2S,1(1S)]-1[D₁]-cis-1,2-Cyclohexanedimethyl bis(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate)

Chemical Property:

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Technology Process of [1R,2S,1(1S)]-1[D₁]-cis-1,2-Cyclohexanedimethyl bis(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate)

There total 3 articles about [1R,2S,1(1S)]-1[D₁]-cis-1,2-Cyclohexanedimethyl bis(2,2,4,4-tetramethyl-1,3-oxazolidine-3-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:

cis-1,2-Cyclohexanedimethyl bis(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate) (235779-96-1) → [1R,2S,1(1S)]-1[D1]-cis-1,2-Cyclohexanedimethyl bis(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate) (235779-97-2)

Guidance literature:

cis-1,2-Cyclohexanedimethyl bis(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate); With sec.-butyllithium; (-)-sparteine; In hexane; cyclohexane; toluene; at -78 ℃; for 4h;

With deuteroacetic acid; In hexane; cyclohexane; toluene; at -78 - 20 ℃; for 16h;

DOI:10.1002/(SICI)1521-3765(19990604)5:6<1905::AID-CHEM1905>3.0.CO;2-4

Reference yield:

cis-1,2-cyclohexanedimethanol (15753-50-1,25712-33-8) → [1R,2S,1(1S)]-1[D1]-cis-1,2-Cyclohexanedimethyl bis(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate) (235779-97-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

1.2: 88 percent / tetrahydrofuran / 16 h / Heating

2.1: sec-BuLi; (-)-sparteine / toluene; cyclohexane; hexane / 4 h / -78 °C

2.2: CH₃CO₂D / toluene; cyclohexane; hexane / 16 h / -78 - 20 °C

With sec.-butyllithium; sodium hydride; (-)-sparteine; In tetrahydrofuran; hexane; cyclohexane; toluene; 1.1: Metallation / 1.2: Acylation / 2.1: Metallation / 2.2: Substitution;

DOI:10.1002/(SICI)1521-3765(19990604)5:6<1905::AID-CHEM1905>3.0.CO;2-4

Reference yield:

cis-1,2-Cyclohexanedimethyl bis[N-(2-hydroxy-1,1-dimethylethyl)carbamate] (235780-27-5) → [1R,2S,1(1S)]-1[D1]-cis-1,2-Cyclohexanedimethyl bis(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate) (235779-97-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 98 percent / K₂CO₃; MeOH / 3 h / Heating

2.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

2.2: 88 percent / tetrahydrofuran / 16 h / Heating

3.1: sec-BuLi; (-)-sparteine / toluene; cyclohexane; hexane / 4 h / -78 °C

3.2: CH₃CO₂D / toluene; cyclohexane; hexane / 16 h / -78 - 20 °C

With methanol; sec.-butyllithium; sodium hydride; potassium carbonate; (-)-sparteine; In tetrahydrofuran; hexane; cyclohexane; toluene; 1.1: deacylation / 2.1: Metallation / 2.2: Acylation / 3.1: Metallation / 3.2: Substitution;

DOI:10.1002/(SICI)1521-3765(19990604)5:6<1905::AID-CHEM1905>3.0.CO;2-4

upstream raw materials:

cis-1,2-Cyclohexanedimethyl bis(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate)

cis-1,2-cyclohexanedimethanol

cis-1,2-Cyclohexanedimethyl bis[N-(2-hydroxy-1,1-dimethylethyl)carbamate]

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