Benzoic acid (1S,2R,3S,4S)-5-benzyloxy-3-hydroxy-1-isopropyl-2,4-dimethyl-pentyl ester

Base Information

Chemical Name:Benzoic acid (1S,2R,3S,4S)-5-benzyloxy-3-hydroxy-1-isopropyl-2,4-dimethyl-pentyl ester
CAS No.:187239-88-9
Molecular Formula:C₂₄H₃₂O₄
Molecular Weight:384.516
Hs Code.:

Synonyms:Benzoic acid (1S,2R,3S,4S)-5-benzyloxy-3-hydroxy-1-isopropyl-2,4-dimethyl-pentyl ester

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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 Benzoic acid (1S,2R,3S,4S)-5-benzyloxy-3-hydroxy-1-isopropyl-2,4-dimethyl-pentyl ester

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Technology Process of Benzoic acid (1S,2R,3S,4S)-5-benzyloxy-3-hydroxy-1-isopropyl-2,4-dimethyl-pentyl ester

There total 2 articles about Benzoic acid (1S,2R,3S,4S)-5-benzyloxy-3-hydroxy-1-isopropyl-2,4-dimethyl-pentyl 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: 86.0%

: 187239-87-8
(2S,4S,5S)-1-Benzyloxy-5-hydroxy-2,4,6-trimethyl-heptan-3-one

: 100-52-7
benzaldehyde

: 187239-88-9
Benzoic acid (1S,2R,3S,4S)-5-benzyloxy-3-hydroxy-1-isopropyl-2,4-dimethyl-pentyl ester

Guidance literature:: With samarium diiodide; In tetrahydrofuran; at 3 ℃; for 16h;
DOI:10.1016/S0040-4039(96)02395-7

Reference yield:

: 116546-78-2
(S)-1-benzyloxy-2-methylpentan-3-one

: 187239-88-9
Benzoic acid (1S,2R,3S,4S)-5-benzyloxy-3-hydroxy-1-isopropyl-2,4-dimethyl-pentyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) cHex₂BCl, Et₃N, 3.) H₂O₂ / 1.) Et₂O, 0 deg C, 2 h, 2.) Et₂O, 0 deg C, 2 h; -20 deg C, 16 h, 3.) pH₇ buffer-MeOH, 0 deg C, 1 h

2: 86 percent / SmI₂ / tetrahydrofuran / 16 h / 3 °C

With samarium diiodide; dicyclohexylboron chloride; dihydrogen peroxide; triethylamine; In tetrahydrofuran;
DOI:10.1016/S0040-4039(96)02395-7

Reference yield:

: 187239-88-9
Benzoic acid (1S,2R,3S,4S)-5-benzyloxy-3-hydroxy-1-isopropyl-2,4-dimethyl-pentyl ester

: 187239-91-4
Benzoic acid (E)-(1S,2R,3S,4S)-3-hydroxy-6-iodo-1-isopropyl-2,4-dimethyl-hex-5-enyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 2,6-lutidine / CH₂Cl₂ / 0.67 h / -78 °C

2: H₂ / Pd(OH)2 / tetrahydrofuran / 16 h / 20 °C

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 90 min, 2.) CH₂Cl₂, -78 deg C, 30 min

4: 73 percent / CrCl₂ / tetrahydrofuran / 16 h / 3 °C

5: 94 percent / PPTS / methanol / 48 h / 20 °C

With 2,6-dimethylpyridine; chromium dichloride; oxalyl dichloride; hydrogen; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/S0040-4039(96)02395-7