4-Undecyne-1,3-diol, 11-(2-hexyl-1,3-dioxolan-2-yl)-2-(phenylmethoxy)-, (2S,3S)-

Base Information

Chemical Name:4-Undecyne-1,3-diol, 11-(2-hexyl-1,3-dioxolan-2-yl)-2-(phenylmethoxy)-, (2S,3S)-
CAS No.:189246-60-4
Molecular Formula:C27H42O5
Molecular Weight:446.627
Hs Code.:

Synonyms:

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Chemical Property of 4-Undecyne-1,3-diol, 11-(2-hexyl-1,3-dioxolan-2-yl)-2-(phenylmethoxy)-, (2S,3S)-

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Technology Process of 4-Undecyne-1,3-diol, 11-(2-hexyl-1,3-dioxolan-2-yl)-2-(phenylmethoxy)-, (2S,3S)-

There total 21 articles about 4-Undecyne-1,3-diol, 11-(2-hexyl-1,3-dioxolan-2-yl)-2-(phenylmethoxy)-, (2S,3S)- 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%

: 7381-30-8
2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane

: 189246-59-1
(16S,17S)-17-benzyloxy-16,18-dihydroxyoctadec-14-yne-7-one

: 189246-60-4
(16S,17S)-17-benzyloxy-16,18-dihydroxyoctadec-14-yne-7-one ethylene acetal

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/ja9730829

Reference yield:

: 189246-52-4
(3RS)-ethyl-3-hydroxynonanethioate

: 189246-60-4
(16S,17S)-17-benzyloxy-16,18-dihydroxyoctadec-14-yne-7-one ethylene acetal

Guidance literature:: Multi-step reaction with 13 steps

1: diisopropylethylamine / CH₂Cl₂ / 10 h / 0 - 20 °C

2: LAH / tetrahydrofuran / 1.5 h / 0 - 20 °C

3: CBr₄; Ph₃P / CH₂Cl₂ / 0.5 h / 0 °C

4: n-BuLi; HMPA / tetrahydrofuran; hexane / 4.5 h / -78 - 0 °C

5: H₂ / Pd/C / ethanol / 20 h / 760 Torr

6: CBr₄; Ph₃P / CH₂Cl₂ / 0.5 h / 0 °C

7: 100 percent / HCl / methanol / 3 h / 50 °C

8: 97 percent / Et₃N / CH₂Cl₂ / 0.25 h / 0 - 20 °C

9: 89 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / 10.5 h / -78 - 0 °C

10: 100 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C

11: 87 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2 h / -78 - 0 °C

12: 100 percent / HCl / tetrahydrofuran / 0.5 h / 20 °C

13: 94 percent / TMSOTf / CH₂Cl₂ / 1 h / 0 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; carbon tetrabromide; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; 1: Etherification / 2: Reduction / 3: Bromination / 4: Addition / 5: Reduction / 6: Bromination / 7: Elimination / 8: Etherification / 9: Addition / 10: Elimination / 11: Swern oxidation / 12: Elimination / 13: Etherification;
DOI:10.1016/S0040-4020(98)00484-0

Reference yield:

: 1-bromo-3-(methoxymethoxy)nonane

: 189246-60-4
(16S,17S)-17-benzyloxy-16,18-dihydroxyoctadec-14-yne-7-one ethylene acetal

Guidance literature:: Multi-step reaction with 10 steps

1: n-BuLi; HMPA / tetrahydrofuran; hexane / 4.5 h / -78 - 0 °C

2: H₂ / Pd/C / ethanol / 20 h / 760 Torr

3: CBr₄; Ph₃P / CH₂Cl₂ / 0.5 h / 0 °C

4: 100 percent / HCl / methanol / 3 h / 50 °C

5: 97 percent / Et₃N / CH₂Cl₂ / 0.25 h / 0 - 20 °C

6: 89 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / 10.5 h / -78 - 0 °C

7: 100 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C

8: 87 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2 h / -78 - 0 °C

9: 100 percent / HCl / tetrahydrofuran / 0.5 h / 20 °C

10: 94 percent / TMSOTf / CH₂Cl₂ / 1 h / 0 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; oxalyl dichloride; carbon tetrabromide; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; 1: Addition / 2: Reduction / 3: Bromination / 4: Elimination / 5: Etherification / 6: Addition / 7: Elimination / 8: Swern oxidation / 9: Elimination / 10: Etherification;
DOI:10.1016/S0040-4020(98)00484-0