ent-2β-(3-phenylpropanoxy)-3α,10β,13-trihydroxy-20-norgibberell-16-ene-7,19-dioic acid 19,10-lactone

Base Information

Chemical Name:ent-2β-(3-phenylpropanoxy)-3α,10β,13-trihydroxy-20-norgibberell-16-ene-7,19-dioic acid 19,10-lactone
CAS No.:1309586-89-7
Molecular Formula:C₂₈H₃₄O₇
Molecular Weight:482.574
Hs Code.:

Synonyms:ent-2β-(3-phenylpropanoxy)-3α,10β,13-trihydroxy-20-norgibberell-16-ene-7,19-dioic acid 19,10-lactone

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Chemical Property of ent-2β-(3-phenylpropanoxy)-3α,10β,13-trihydroxy-20-norgibberell-16-ene-7,19-dioic acid 19,10-lactone

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Technology Process of ent-2β-(3-phenylpropanoxy)-3α,10β,13-trihydroxy-20-norgibberell-16-ene-7,19-dioic acid 19,10-lactone

There total 8 articles about ent-2β-(3-phenylpropanoxy)-3α,10β,13-trihydroxy-20-norgibberell-16-ene-7,19-dioic acid 19,10-lactone 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: 70.0%

: 1309586-88-6
ent-10β,13-dihydroxy-2β-(3-phenylpropanoxy)-3α-tetrahydropyran-2-yloxy-20-norgibberell-16-ene-7,19-dioic acid 7-methyl ester 19,10-lactone

: 1309586-87-5
ent-3α,13-bis-tetrahydropyran-2-yloxy-10β-hydroxy-2β-(3-phenylpropanoxy)-20-norgibberell-16-ene-7,19-dioic acid 7-methyl ester 19,10-lactone

: 1309586-89-7
ent-2β-(3-phenylpropanoxy)-3α,10β,13-trihydroxy-20-norgibberell-16-ene-7,19-dioic acid 19,10-lactone

Guidance literature:: ent-10β,13-dihydroxy-2β-(3-phenylpropanoxy)-3α-tetrahydropyran-2-yloxy-20-norgibberell-16-ene-7,19-dioic acid 7-methyl ester 19,10-lactone; ent-3α,13-bis-tetrahydropyran-2-yloxy-10β-hydroxy-2β-(3-phenylpropanoxy)-20-norgibberell-16-ene-7,19-dioic acid 7-methyl ester 19,10-lactone; With N,N,N,N,N,N-hexamethylphosphoric triamide; 1-thiopropane; sodium hydride; for 16h;

With pyridinium p-toluenesulfonate; In ethanol; at 60 ℃; for 14h;
DOI:10.1071/CH10441

Reference yield:

: 1309586-73-9
C₂₂H₂₆O₈

: 1309586-89-7
ent-2β-(3-phenylpropanoxy)-3α,10β,13-trihydroxy-20-norgibberell-16-ene-7,19-dioic acid 19,10-lactone

Guidance literature:: Multi-step reaction with 7 steps

1.1: Oxone; 1,1,1-trifluoro-2-propanone; edetate disodium; sodium hydrogencarbonate / water; acetonitrile / 15 h / 0 °C

2.1: water; potassium carbonate / tetrahydrofuran; ethanol / 20 h

3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 0 - 20 °C

4.1: potassium tert-butylate / tetrahydrofuran; tert-butyl alcohol / -78 - 20 °C

4.2: 2.83 h

4.3: 0.42 h

5.1: tris(pentafluorophenyl)borate / 1,2-dichloro-ethane / 55 °C

6.1: pyridinium p-toluenesulfonate / dichloromethane / 53 h

7.1: N,N,N,N,N,N-hexamethylphosphoric triamide; 1-thiopropane; sodium hydride / 16 h

7.2: 14 h / 60 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; Oxone; 1-thiopropane; 1,1,1-trifluoro-2-propanone; tris(pentafluorophenyl)borate; potassium tert-butylate; water; pyridinium p-toluenesulfonate; edetate disodium; sodium hydride; sodium hydrogencarbonate; potassium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile; tert-butyl alcohol; 4.1: Wittig reaction / 4.2: Wittig reaction;
DOI:10.1071/CH10441

Reference yield:

: 1309586-72-8
ent-13-acetoxy-2α,3α-epoxy-10β-hydroxy-16-oxo-17,20-dinorgibberellane-7,19-dioic acid 7-methoxymethyl ester 19,10-lactone

: 1309586-89-7
ent-2β-(3-phenylpropanoxy)-3α,10β,13-trihydroxy-20-norgibberell-16-ene-7,19-dioic acid 19,10-lactone

Guidance literature:: Multi-step reaction with 6 steps

1.1: water; potassium carbonate / tetrahydrofuran; ethanol / 20 h

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 0 - 20 °C

3.1: potassium tert-butylate / tetrahydrofuran; tert-butyl alcohol / -78 - 20 °C

3.2: 2.83 h

3.3: 0.42 h

4.1: tris(pentafluorophenyl)borate / 1,2-dichloro-ethane / 55 °C

5.1: pyridinium p-toluenesulfonate / dichloromethane / 53 h

6.1: N,N,N,N,N,N-hexamethylphosphoric triamide; 1-thiopropane; sodium hydride / 16 h

6.2: 14 h / 60 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; 1-thiopropane; tris(pentafluorophenyl)borate; potassium tert-butylate; water; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; dichloromethane; 1,2-dichloro-ethane; tert-butyl alcohol; 3.1: Wittig reaction / 3.2: Wittig reaction;
DOI:10.1071/CH10441