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

Base Information

• Chemical Name: (2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-14-O-(tert-butyldimethylsilyl)-(4E)-tetradecene-1,3,14-triol
• CAS No.: 608880-36-0
• Molecular Formula: C₃₉H₅₉NO₇Si
• Molecular Weight: 681.985
• Mol file: 608880-36-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-14-O-(tert-butyldimethylsilyl)-(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: 91.0%

benzoic acid anhydride (93-97-0) + (2S,3R)-2-(tert-butoxycarbonylamino)-14-O-(tert-butyldimethylsilyl)-(4E)-tetradecene-1,3,14-triol (608880-35-9) → (2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-14-O-(tert-butyldimethylsilyl)-(4E)-tetradecene-1,3,14-triol (608880-36-0)

Guidance literature:

With pyridine; dmap; at 20 ℃;

DOI:10.1021/jo034828q

Reference yield:

undec-10-yn-1-ol (2774-84-7) → (2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-14-O-(tert-butyldimethylsilyl)-(4E)-tetradecene-1,3,14-triol (608880-36-0)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1021/jo034828q

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-14-O-(tert-butyldimethylsilyl)-(4E)-tetradecene-1,3,14-triol (608880-36-0)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With pyridine; dmap; triethylamine; In 1,4-dioxane; water;

DOI:10.1021/jo034828q

upstream raw materials:

benzoic acid anhydride

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

undec-10-yn-1-ol

di-tert-butyl dicarbonate

Downstream raw materials:

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

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

(2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-14-O-[4'-[3-(trifluoromethyl)diaziridin-3-yl]phenyl]-(4E)-tetradecene-1,3,14-triol

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