(2S,4S,6R)-ethyl 4-hydroxy-4,6-diphenyltetrahydro-2H-pyran-2-carboxylate

Base Information

• Chemical Name: (2S,4S,6R)-ethyl 4-hydroxy-4,6-diphenyltetrahydro-2H-pyran-2-carboxylate
• CAS No.: 1402854-03-8
• Molecular Formula: C₂₀H₂₂O₄
• Molecular Weight: 326.392
• Mol file: 1402854-03-8.mol

Synonyms:(2S,4S,6R)-ethyl 4-hydroxy-4,6-diphenyltetrahydro-2H-pyran-2-carboxylate

Chemical Property of (2S,4S,6R)-ethyl 4-hydroxy-4,6-diphenyltetrahydro-2H-pyran-2-carboxylate

Chemical Property:

Purity/Quality:

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Technology Process of (2S,4S,6R)-ethyl 4-hydroxy-4,6-diphenyltetrahydro-2H-pyran-2-carboxylate

There total 5 articles about (2S,4S,6R)-ethyl 4-hydroxy-4,6-diphenyltetrahydro-2H-pyran-2-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:

[18O]-benzaldehyde (55076-26-1) + ethyl (S)-2-hydroxy-4-phenylpent-4-enoate (208242-82-4) → (2S,4S,6R)-ethyl 4-hydroxy-4,6-diphenyltetrahydro-2H-pyran-2-carboxylate (1402854-66-3) + (2S,4S,6R)-ethyl 4-hydroxy-4,6-diphenyltetrahydro-2H-pyran-2-carboxylate (1402854-03-8)

Guidance literature:

With iron(III) chloride; tert-butyldimethylsilyl chloride; In dichloromethane; at 10 ℃; Overall yield = 74 %; enantioselective reaction;

DOI:10.1021/ja3062002

Reference yield:

benzaldehyde (100-52-7) + ethyl (S)-2-hydroxy-4-phenylpent-4-enoate (208242-82-4) → (2S,4S,6R)-ethyl 4-hydroxy-4,6-diphenyltetrahydro-2H-pyran-2-carboxylate (1402854-66-3) + (2S,4S,6R)-ethyl 4-hydroxy-4,6-diphenyltetrahydro-2H-pyran-2-carboxylate (1402854-03-8)

Guidance literature:

With iron(III) chloride; tert-butyldimethylsilyl chloride; ¹⁸O-labeled water; In dichloromethane; at 10 ℃; Overall yield = 70 %; enantioselective reaction;

DOI:10.1021/ja3062002

Reference yield:

benzaldehyde (100-52-7) + ethyl (S)-2-hydroxy-4-phenylpent-4-enoate (208242-82-4) → (2S,4S,6R)-ethyl 4-hydroxy-4,6-diphenyltetrahydro-2H-pyran-2-carboxylate (1402854-03-8) + ethyl 4-hydroxy-4,6-diphenyltetrahydro-2H-pyran-2-carboxylate

Guidance literature:

With iron(III) chloride; tert-butyldimethylsilyl chloride; In dichloromethane; at 10 ℃; for 12h; stereoselective reaction;

DOI:10.1021/ja3062002

upstream raw materials:

[¹⁸O]-benzaldehyde

ethyl (S)-2-hydroxy-4-phenylpent-4-enoate

benzaldehyde

isopropenylbenzene