(2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-(4E)-tetradecene-1,3,14-triol

Base Information

Chemical Name:(2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-(4E)-tetradecene-1,3,14-triol
CAS No.:608880-37-1
Molecular Formula:C₃₃H₄₅NO₇
Molecular Weight:567.723
Hs Code.:

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

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

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

There total 7 articles about (2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-(4E)-tetradecene-1,3,14-triol 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: 73.0%

: 608880-36-0
(2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-14-O-(tert-butyldimethylsilyl)-(4E)-tetradecene-1,3,14-triol

: 608880-37-1
(2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-(4E)-tetradecene-1,3,14-triol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;
DOI:10.1021/jo034828q

Reference yield:

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

: 608880-37-1
(2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-(4E)-tetradecene-1,3,14-triol

Guidance literature:: Multi-step reaction with 6 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

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; tetrabutyl ammonium fluoride; lithium; ethylamine; triethylamine; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; 3.1: Birch reduction;
DOI:10.1021/jo034828q

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 608880-37-1
(2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-(4E)-tetradecene-1,3,14-triol

Guidance literature:: Multi-step reaction with 3 steps

1: 3.97 g / Et₃N / dioxane; H₂O / 20 °C

2: 91 percent / (dimethylamino)pyridine; pyridine / 20 °C

3: 73 percent / TBAF / tetrahydrofuran / 20 °C

With pyridine; dmap; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; 1,4-dioxane; water;
DOI:10.1021/jo034828q