O^α-(tetrahydropyran-2-yl)-D-mandelic acid

Base Information

• Chemical Name: O^α-(tetrahydropyran-2-yl)-D-mandelic acid
• CAS No.: 156557-10-7
• Molecular Formula: C₁₃H₁₆O₄
• Molecular Weight: 236.268
• Mol file: 156557-10-7.mol

Synonyms:O^α-(tetrahydropyran-2-yl)-D-mandelic acid

Chemical Property of O^α-(tetrahydropyran-2-yl)-D-mandelic acid

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of O^α-(tetrahydropyran-2-yl)-D-mandelic acid

There total 2 articles about O^α-(tetrahydropyran-2-yl)-D-mandelic acid 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:

3,4-dihydro-2H-pyran (110-87-2) + (R)-Mandelic Acid (611-71-2) → Oα-(tetrahydropyran-2-yl)-D-mandelic acid (156557-10-7)

Guidance literature:

With toluene-4-sulfonic acid; In chloroform; for 1h; Yield given; Ambient temperature;

DOI:10.1016/S0040-4039(98)02566-0

Reference yield:

(1R)-S-ethyl [1-phenyl-1-tetrahydropyran-(2RS)-2-yloxy]-thioacetate (157982-28-0) → Oα-(tetrahydropyran-2-yl)-D-mandelic acid (156557-10-7)

Guidance literature:

With lithium hydroperoxide; In tetrahydrofuran; water;

DOI:10.1016/S0040-4020(97)01010-7

Reference yield: 97.0%

RS-mexiletine (31828-71-4) + Oα-(tetrahydropyran-2-yl)-D-mandelic acid (156557-10-7) → (2RS)-N-(1-(2',6'-dimethylphenoxy)-2-propyl)-tetrahydropyranyl-(R)-mandelamide (252049-70-0)

Guidance literature:

With dicyclohexyl-carbodiimide; In ethyl acetate; at 20 ℃; for 18h;

DOI:10.1016/S0957-4166(99)00311-0

upstream raw materials:

(1R)-S-ethyl [1-phenyl-1-tetrahydropyran-(2RS)-2-yloxy]-thioacetate

3,4-dihydro-2H-pyran

(R)-Mandelic Acid

Downstream raw materials:

H-[L-Val-D-Man-D-Val-L-Lac]3-OH

(2RS)-N-(1-(2',6'-dimethylphenoxy)-2-propyl)-tetrahydropyranyl-(R)-mandelamide

Refernces

• 1、 Kuisle, Oliver,Quinoa, Emilio,Riguera, Ricardo. "A general methodology for automated solid-phase synthesis of depsides and depsipeptides. Preparation of a valinomycin analogue". . p. 8063 - 8075. Retrieved 2007/10/03.