benzoic acid (2R,3S)-2-hydroxymethyl-2,6,6-trimethyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: benzoic acid (2R,3S)-2-hydroxymethyl-2,6,6-trimethyl-tetrahydro-pyran-3-yl ester
• CAS No.: 434956-77-1
• Molecular Formula: C₁₆H₂₂O₄
• Molecular Weight: 278.348

Synonyms:benzoic acid (2R,3S)-2-hydroxymethyl-2,6,6-trimethyl-tetrahydro-pyran-3-yl ester

Chemical Property of benzoic acid (2R,3S)-2-hydroxymethyl-2,6,6-trimethyl-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of benzoic acid (2R,3S)-2-hydroxymethyl-2,6,6-trimethyl-tetrahydro-pyran-3-yl ester

There total 6 articles about benzoic acid (2R,3S)-2-hydroxymethyl-2,6,6-trimethyl-tetrahydro-pyran-3-yl 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: 44.0%

benzoic acid (1S,2R)-4-hydroxy-4-methyl-1-(2-methyl-oxiranyl)-pentyl ester (434956-20-4) → benzoic acid (2R,3S)-3-hydroxy-3,7,7,7-trimethyl-oxepan-4-yl ester + benzoic acid (2R,2'R)-2-(5',5'-dimethyl-tetrahydro-furan-2'-yl)-2-hydroxy-propyl ester + benzoic acid (2R,3S)-2-hydroxymethyl-2,6,6-trimethyl-tetrahydro-pyran-3-yl ester (434956-77-1) + benzoic acid (2S,3S)-2,3,6-trihydroxy-2,6-dimethyl-heptyl ester (434956-66-8)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; at -40 - 20 ℃; for 12h; Further byproducts given;

DOI:10.1055/s-2002-19792

Reference yield: 10.0%

benzoic acid (1S,2R)-4-hydroxy-4-methyl-1-(2-methyl-oxiranyl)-pentyl ester (434956-20-4) → benzoic acid (2R,3S)-3-hydroxy-3,7,7,7-trimethyl-oxepan-4-yl ester + benzoic acid (2R,3S)-2-hydroxymethyl-2,6,6-trimethyl-tetrahydro-pyran-3-yl ester (434956-77-1) + benzoic acid (1S,1S')-1-(1',2'-dihydroxy-1'-methyl-ethyl)-4-hydroxy-4-methyl-pentyl ester (434956-61-3) + benzoic acid (2S,3S)-2,3,6-trihydroxy-2,6-dimethyl-heptyl ester (434956-66-8)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; at -40 - 20 ℃; for 12h; Further byproducts given;

DOI:10.1055/s-2002-19792

Reference yield:

benzoyl chloride (98-88-4) → benzoic acid (2R,3S)-2-hydroxymethyl-2,6,6-trimethyl-tetrahydro-pyran-3-yl ester (434956-77-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 95 percent / tetrahydrofuran; hexane / 2 h / 0 °C

2.1: MCPBA / CH₂Cl₂ / 0 °C

3.1: 44 percent / CSA / CH₂Cl₂ / 12 h / -40 - 20 °C

With n-butyllithium; camphor-10-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1055/s-2002-19792

upstream raw materials:

benzoic acid (1S,2R)-4-hydroxy-4-methyl-1-(2-methyl-oxiranyl)-pentyl ester

benzoyl chloride

(5S)-2,6-Dimethylhept-6-ene-2,5-diol

benzoic acid (1S)-1-(3-hydroxy-3-methyl-butyl)-2-methyl-allyl ester

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