(2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-14-O-(4'-(trifluoroacetyl)phenyl)-(4E)-tetradecene-1,3,14-triol O-tosyl oxime

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Chemical Name:(2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-14-O-(4'-(trifluoroacetyl)phenyl)-(4E)-tetradecene-1,3,14-triol O-tosyl oxime
CAS No.:608880-43-9
Molecular Formula:C₄₈H₅₅F₃N₂O₁₀S
Molecular Weight:909.033
Hs Code.:

Synonyms:(2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-14-O-(4'-(trifluoroacetyl)phenyl)-(4E)-tetradecene-1,3,14-triol O-tosyl oxime

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Chemical Property of (2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-14-O-(4'-(trifluoroacetyl)phenyl)-(4E)-tetradecene-1,3,14-triol O-tosyl oxime

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Technology Process of (2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-14-O-(4'-(trifluoroacetyl)phenyl)-(4E)-tetradecene-1,3,14-triol O-tosyl oxime

There total 12 articles about (2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-14-O-(4'-(trifluoroacetyl)phenyl)-(4E)-tetradecene-1,3,14-triol O-tosyl oxime 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: 99.0%

: 98-59-9
p-toluenesulfonyl chloride

: 608880-42-8
(2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-14-O-(4'-(trifluoroacetyl)phenyl)-(4E)-tetradecene-1,3,14-triol oxime

: 608880-43-9
(2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-14-O-(4'-(trifluoroacetyl)phenyl)-(4E)-tetradecene-1,3,14-triol O-tosyl oxime

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/jo034828q

Reference yield:

: 2774-84-7
undec-10-yn-1-ol

: 608880-43-9
(2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-14-O-(4'-(trifluoroacetyl)phenyl)-(4E)-tetradecene-1,3,14-triol O-tosyl oxime

Guidance literature:: Multi-step reaction with 9 steps

1.1: 98 percent / imidazole / CH₂Cl₂ / 20 °C

2.1: n-BuLi; HMPA / tetrahydrofuran; hexane / 2.5 h / -78 °C

2.2: 67 percent / tetrahydrofuran; hexane / 2.5 h / -78 °C

3.1: lithium; EtNH₂ / tetrahydrofuran / 4 h / -78 °C

4.1: 3.97 g / Et₃N / dioxane; H₂O / 20 °C

5.1: 91 percent / (dimethylamino)pyridine; pyridine / 20 °C

6.1: 73 percent / TBAF / tetrahydrofuran / 20 °C

7.1: 74 percent / DIAD; Ph₃P / CH₂Cl₂ / 0 - 20 °C

8.1: 99 percent / hydroxylamine hydrochloride; pyridine / ethanol / 12 h / 50 - 60 °C

9.1: 99 percent / triethylamine; DMAP / CH₂Cl₂ / 0 - 20 °C

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; di-isopropyl azodicarboxylate; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; lithium; ethylamine; triethylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; ethanol; hexane; dichloromethane; water; 3.1: Birch reduction / 7.1: Mitsunobu reaction;
DOI:10.1021/jo034828q

Reference yield:

: 1823-63-8
2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one

: 608880-43-9
(2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-14-O-(4'-(trifluoroacetyl)phenyl)-(4E)-tetradecene-1,3,14-triol O-tosyl oxime

Guidance literature:: Multi-step reaction with 3 steps

1: 74 percent / DIAD; Ph₃P / CH₂Cl₂ / 0 - 20 °C

2: 99 percent / hydroxylamine hydrochloride; pyridine / ethanol / 12 h / 50 - 60 °C

3: 99 percent / triethylamine; DMAP / CH₂Cl₂ / 0 - 20 °C

With pyridine; dmap; di-isopropyl azodicarboxylate; hydroxylamine hydrochloride; triethylamine; triphenylphosphine; In ethanol; dichloromethane; 1: Mitsunobu reaction;
DOI:10.1021/jo034828q