(1S,2S,3R,4S,5R,8R,9S,10R,13S)-4-(acetoxy)-2-(benzoyloxy)-5,20-epoxy-1,9,10,13-tetrahydroxytax-11-ene

Base Information

Chemical Name:(1S,2S,3R,4S,5R,8R,9S,10R,13S)-4-(acetoxy)-2-(benzoyloxy)-5,20-epoxy-1,9,10,13-tetrahydroxytax-11-ene
CAS No.:184586-81-0
Molecular Formula:C₂₉H₃₈O₉
Molecular Weight:530.615
Hs Code.:

Synonyms:(1S,2S,3R,4S,5R,8R,9S,10R,13S)-4-(acetoxy)-2-(benzoyloxy)-5,20-epoxy-1,9,10,13-tetrahydroxytax-11-ene

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Chemical Property of (1S,2S,3R,4S,5R,8R,9S,10R,13S)-4-(acetoxy)-2-(benzoyloxy)-5,20-epoxy-1,9,10,13-tetrahydroxytax-11-ene

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Technology Process of (1S,2S,3R,4S,5R,8R,9S,10R,13S)-4-(acetoxy)-2-(benzoyloxy)-5,20-epoxy-1,9,10,13-tetrahydroxytax-11-ene

There total 7 articles about (1S,2S,3R,4S,5R,8R,9S,10R,13S)-4-(acetoxy)-2-(benzoyloxy)-5,20-epoxy-1,9,10,13-tetrahydroxytax-11-ene 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: 58.0%

: 173422-30-5
(1S,2S,3R,4S,5R,7S,8R,10R,13S)-4-acetoxy-2-benzoyloxy-5,20-epoxy-9-oxo-1,10,13-trihydroxytax-11-ene

: 184586-81-0
(1S,2S,3R,4S,5R,8R,9S,10R,13S)-4-(acetoxy)-2-(benzoyloxy)-5,20-epoxy-1,9,10,13-tetrahydroxytax-11-ene

Guidance literature:: With borane-THF; In tetrahydrofuran; at 0 ℃;
DOI:10.1016/S0960-894X(02)00628-5

Reference yield:

: 32981-86-5,172018-16-5
10-deacetylbaccatin III

: 184586-81-0
(1S,2S,3R,4S,5R,8R,9S,10R,13S)-4-(acetoxy)-2-(benzoyloxy)-5,20-epoxy-1,9,10,13-tetrahydroxytax-11-ene

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / Tf₂O; DMAP / 0 °C

2: 75 percent / DBU / benzene; tetrahydrofuran / 20 °C

3: 46 percent / n-Bu₃SnH; AIBN / dioxane / 80 °C

4: 61 percent / N₂H₄ / ethanol / 20 °C

5: 58 percent / BH₃*THF / tetrahydrofuran / 0 °C

With dmap; borane-THF; 2,2'-azobis(isobutyronitrile); trifluoromethylsulfonic anhydride; tri-n-butyl-tin hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; hydrazine; In tetrahydrofuran; 1,4-dioxane; ethanol; benzene;
DOI:10.1016/S0960-894X(02)00628-5

Reference yield:

: 272129-02-9
(1S,2S,3R,4S,5R,7S,8R,10R,13S)-4-acetoxy-2-benzoyloxy-5,20-epoxy-9-oxo-1,10,13-trihydroxytax-6,11-diene

: 184586-81-0
(1S,2S,3R,4S,5R,8R,9S,10R,13S)-4-(acetoxy)-2-(benzoyloxy)-5,20-epoxy-1,9,10,13-tetrahydroxytax-11-ene

Guidance literature:: Multi-step reaction with 2 steps

1.1: ammonium formate / palladium 10% on activated carbon / ethanol; water / 40 - 60 °C / Inert atmosphere

2.1: borane-THF / tetrahydrofuran / -10 - 0 °C / Inert atmosphere

2.2: Cooling with ice

With borane-THF; ammonium formate; palladium 10% on activated carbon; In tetrahydrofuran; ethanol; water;