(2E,4E)-(6S,7S,8S)-7-Hydroxy-6,8-dimethyl-9-trityloxy-nona-2,4-dienoic acid ethyl ester

Base Information

Chemical Name:(2E,4E)-(6S,7S,8S)-7-Hydroxy-6,8-dimethyl-9-trityloxy-nona-2,4-dienoic acid ethyl ester
CAS No.:186885-55-2
Molecular Formula:C₃₂H₃₆O₄
Molecular Weight:484.635
Hs Code.:

Synonyms:(2E,4E)-(6S,7S,8S)-7-Hydroxy-6,8-dimethyl-9-trityloxy-nona-2,4-dienoic acid ethyl ester

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Chemical Property of (2E,4E)-(6S,7S,8S)-7-Hydroxy-6,8-dimethyl-9-trityloxy-nona-2,4-dienoic acid ethyl ester

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Technology Process of (2E,4E)-(6S,7S,8S)-7-Hydroxy-6,8-dimethyl-9-trityloxy-nona-2,4-dienoic acid ethyl ester

There total 7 articles about (2E,4E)-(6S,7S,8S)-7-Hydroxy-6,8-dimethyl-9-trityloxy-nona-2,4-dienoic acid ethyl 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:

: 186885-64-3
(2E,4E)-(6S,7S,8S)-6,8-Dimethyl-7-triethylsilanyloxy-9-trityloxy-nona-2,4-dienoic acid ethyl ester

: 186885-55-2
(2E,4E)-(6S,7S,8S)-7-Hydroxy-6,8-dimethyl-9-trityloxy-nona-2,4-dienoic acid ethyl ester

Guidance literature:: With pyridine hydrogenfluoride; In tetrahydrofuran; at 0 ℃; Yield given;
DOI:10.1021/jo9621884

Reference yield:

: 186885-62-1
(2S,3R)-2,4-Dimethyl-3-triethylsilanyloxy-pent-4-en-1-ol

: 186885-55-2
(2E,4E)-(6S,7S,8S)-7-Hydroxy-6,8-dimethyl-9-trityloxy-nona-2,4-dienoic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: DMAP, Et₃N / CH₂Cl₂

2: 1.) 9-BBN dimer, 2.) H₂O₂ / 1.) THF, 0 deg C

3: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, 2.) -78 deg C

4: 1.) LiHMDS / 1.) THF, -78 deg C

5: HF*pyr / tetrahydrofuran / 0 °C

With dmap; oxalyl dichloride; dihydrogen peroxide; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; dimeric 9-borabicyclo[3.3.1]nonane; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo9621884

Reference yield:

: 186885-60-9
[[3-(2R,3R)-4R]-3-(3-hydroxy-2,4-dimethyl-1-oxopent-4-enyl)-4-(phenylmethyl)]-2-oxazolidinone

: 186885-55-2
(2E,4E)-(6S,7S,8S)-7-Hydroxy-6,8-dimethyl-9-trityloxy-nona-2,4-dienoic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 2,6-lutidine / CH₂Cl₂ / 0 °C

2: LiBH₄ / diethyl ether; H₂O / 25 °C

3: DMAP, Et₃N / CH₂Cl₂

4: 1.) 9-BBN dimer, 2.) H₂O₂ / 1.) THF, 0 deg C

5: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, 2.) -78 deg C

6: 1.) LiHMDS / 1.) THF, -78 deg C

7: HF*pyr / tetrahydrofuran / 0 °C

With 2,6-dimethylpyridine; dmap; lithium borohydride; oxalyl dichloride; dihydrogen peroxide; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; dimeric 9-borabicyclo[3.3.1]nonane; In tetrahydrofuran; diethyl ether; dichloromethane; water;
DOI:10.1021/jo9621884