Technology Process of (1R,2S,3S,4S)-4-(benzyloxymethyl)-2,3-dihydroxycyclopentyl benzoate
There total 4 articles about (1R,2S,3S,4S)-4-(benzyloxymethyl)-2,3-dihydroxycyclopentyl benzoate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
AD-mix α;
In
water; tert-butyl alcohol;
at 0 ℃;
for 12h;
optical yield given as %de;
DOI:10.1002/ejoc.201001473
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
1.2: 0 °C / Inert atmosphere
2.1: L-diisopinocampheylborane / tetrahydrofuran / -78 - 0 °C / Inert atmosphere
2.2: 4 h / 0 °C
3.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C
4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
4.2: oxone / 6 h / 0 °C
5.1: potassium tert-butylate / N,N-dimethyl-formamide / 1 h / Reflux
6.1: di-isopropyl azodicarboxylate; triphenylphosphine / diethyl ether / 0.5 h / 0 °C / Inert atmosphere
6.2: 0 - 20 °C / Inert atmosphere
7.1: AD-mix α / water; tert-butyl alcohol / 12 h / 0 °C
With
di-isopropyl azodicarboxylate; potassium tert-butylate; sodium hydride; triethylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; L-diisopinocampheylborane;
In
tetrahydrofuran; diethyl ether; water; N,N-dimethyl-formamide; tert-butyl alcohol;
2.1: Hydroboration reaction / 4.1: Hydroboration reaction / 6.1: Mitsunobu reaction / 6.2: Mitsunobu reaction / 7.1: Sharpless dihydroxylation;
DOI:10.1002/ejoc.201001473
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C
2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
2.2: oxone / 6 h / 0 °C
3.1: potassium tert-butylate / N,N-dimethyl-formamide / 1 h / Reflux
4.1: di-isopropyl azodicarboxylate; triphenylphosphine / diethyl ether / 0.5 h / 0 °C / Inert atmosphere
4.2: 0 - 20 °C / Inert atmosphere
5.1: AD-mix α / water; tert-butyl alcohol / 12 h / 0 °C
With
di-isopropyl azodicarboxylate; potassium tert-butylate; triethylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine;
In
tetrahydrofuran; diethyl ether; water; N,N-dimethyl-formamide; tert-butyl alcohol;
2.1: Hydroboration reaction / 4.1: Mitsunobu reaction / 4.2: Mitsunobu reaction / 5.1: Sharpless dihydroxylation;
DOI:10.1002/ejoc.201001473
