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

Base Information

Chemical Name:Benzoic acid (E)-(1S,2R,3S,4S)-3-hydroxy-6-iodo-1-isopropyl-2,4-dimethyl-hex-5-enyl ester
CAS No.:187239-91-4
Molecular Formula:C₁₈H₂₅IO₃
Molecular Weight:416.299
Hs Code.:

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

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Chemical Property of Benzoic acid (E)-(1S,2R,3S,4S)-3-hydroxy-6-iodo-1-isopropyl-2,4-dimethyl-hex-5-enyl ester

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Technology Process of Benzoic acid (E)-(1S,2R,3S,4S)-3-hydroxy-6-iodo-1-isopropyl-2,4-dimethyl-hex-5-enyl ester

There total 7 articles about Benzoic acid (E)-(1S,2R,3S,4S)-3-hydroxy-6-iodo-1-isopropyl-2,4-dimethyl-hex-5-enyl 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: 94.0%

: 187239-90-3
Benzoic acid (E)-(1S,2S,3S,4S)-6-iodo-1-isopropyl-2,4-dimethyl-3-triethylsilanyloxy-hex-5-enyl 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:: With pyridinium p-toluenesulfonate; In methanol; at 20 ℃; for 48h;
DOI:10.1016/S0040-4039(96)02395-7

Reference yield:

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

: 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 6 steps

1: 86 percent / SmI₂ / tetrahydrofuran / 16 h / 3 °C

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

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

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

5: 73 percent / CrCl₂ / tetrahydrofuran / 16 h / 3 °C

6: 94 percent / PPTS / methanol / 48 h / 20 °C

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

Reference yield:

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

: 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 7 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

3: 2,6-lutidine / CH₂Cl₂ / 0.67 h / -78 °C

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

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

6: 73 percent / CrCl₂ / tetrahydrofuran / 16 h / 3 °C

7: 94 percent / PPTS / methanol / 48 h / 20 °C

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