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Cas Database

6996-36-7

6996-36-7

Identification

Synonyms:3β-(toluene-4-sulfonyloxy)-pregna-5,16-dien-20-one

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Relevant articles and documentsAll total 1 Articles be found

Concise Synthesis of the Core Structures of Saundersiosides

Cheng, Shou-Ling,Jiang, Xiao-Ling,Shi, Yong,Tian, Wei-Sheng

, p. 2346 - 2349 (2015)

A divergent synthesis of three core pentacyclic lactones of nine rearranged cholestane sapogenins, saundersiosides A-H (1-8) and candicanoside A (9), is reported. Key features include a one-flask CBS reduction/Brown hydroboration-oxidation, a SmI2/s

Process route upstream and downstream products

Process route

16-dehydropregnenolone
1162-53-4

16-dehydropregnenolone

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

3β-(toluene-4-sulfonyloxy)-pregna-5,16-dien-20-one
6996-36-7

3β-(toluene-4-sulfonyloxy)-pregna-5,16-dien-20-one

Conditions
Conditions Yield
With pyridine; dmap; at 20 ℃; for 28h; Inert atmosphere;
89%
3β-hydroxypregn-5-ene-16,20-dione
911442-53-0

3β-hydroxypregn-5-ene-16,20-dione

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

3β-(toluene-4-sulfonyloxy)-pregna-5,16-dien-20-one
6996-36-7

3β-(toluene-4-sulfonyloxy)-pregna-5,16-dien-20-one

Conditions
Conditions Yield
3β-(toluene-4-sulfonyloxy)-pregna-5,16-dien-20-one
6996-36-7

3β-(toluene-4-sulfonyloxy)-pregna-5,16-dien-20-one

3β-hydroxy-16α,17α-epoxypregn-5-en-20-one
974-23-2

3β-hydroxy-16α,17α-epoxypregn-5-en-20-one

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: potassium acetate
2: benzene / Erwaermen des erhaltenen 16α,17-Epoxy-6β-methoxy-3α,5α-cyclo-pregnan-20-ons mit Schwefelsaeure enthaltendem wss.Dioxan
With potassium acetate; benzene;
3β-(toluene-4-sulfonyloxy)-pregna-5,16-dien-20-one
6996-36-7

3β-(toluene-4-sulfonyloxy)-pregna-5,16-dien-20-one

16α,17α-epoxyprogesterone
1097-51-4,16356-47-1

16α,17α-epoxyprogesterone

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: potassium acetate
2: benzene / Erwaermen des erhaltenen 16α,17-Epoxy-6β-methoxy-3α,5α-cyclo-pregnan-20-ons mit Schwefelsaeure enthaltendem wss.Dioxan
3: cyclohexanone; aluminium isopropylate; toluene
With potassium acetate; cyclohexanone; aluminum isopropoxide; toluene; benzene;
3β-(toluene-4-sulfonyloxy)-pregna-5,16-dien-20-one
6996-36-7

3β-(toluene-4-sulfonyloxy)-pregna-5,16-dien-20-one

C<sub>38</sub>H<sub>54</sub>O<sub>3</sub>Si

C38H54O3Si

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: pyridine / 4 h / Inert atmosphere; Reflux
2: dimethylsulfide borane complex / tetrahydrofuran / 20 °C / Inert atmosphere; Cooling
3: dihydrogen peroxide; sodium hydroxide / tetrahydrofuran; water / 25 °C / Inert atmosphere
4: N-ethyl-N,N-diisopropylamine / dichloromethane / 10 h / 0 - 20 °C / Inert atmosphere
With pyridine; dimethylsulfide borane complex; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; dichloromethane; water; 2: |Corey-Bakshi-Shibata Reduction / 3: |Brown Hydroboration;
3β-(toluene-4-sulfonyloxy)-pregna-5,16-dien-20-one
6996-36-7

3β-(toluene-4-sulfonyloxy)-pregna-5,16-dien-20-one

C<sub>38</sub>H<sub>52</sub>O<sub>4</sub>Si

C38H52O4Si

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: pyridine / 4 h / Inert atmosphere; Reflux
2: dimethylsulfide borane complex / tetrahydrofuran / 20 °C / Inert atmosphere; Cooling
3: dihydrogen peroxide; sodium hydroxide / tetrahydrofuran; water / 25 °C / Inert atmosphere
4: N-ethyl-N,N-diisopropylamine / dichloromethane / 10 h / 0 - 20 °C / Inert atmosphere
5: [bis(acetoxy)iodo]benzene; calcium carbonate; iodine / cyclohexane / 1.5 h / Inert atmosphere; Irradiation; Reflux
With pyridine; [bis(acetoxy)iodo]benzene; dimethylsulfide borane complex; dihydrogen peroxide; iodine; N-ethyl-N,N-diisopropylamine; calcium carbonate; sodium hydroxide; In tetrahydrofuran; dichloromethane; cyclohexane; water; 2: |Corey-Bakshi-Shibata Reduction / 3: |Brown Hydroboration;
3β-(toluene-4-sulfonyloxy)-pregna-5,16-dien-20-one
6996-36-7

3β-(toluene-4-sulfonyloxy)-pregna-5,16-dien-20-one

C<sub>38</sub>H<sub>54</sub>O<sub>4</sub>Si

C38H54O4Si

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1: pyridine / 4 h / Inert atmosphere; Reflux
2: dimethylsulfide borane complex / tetrahydrofuran / 20 °C / Inert atmosphere; Cooling
3: dihydrogen peroxide; sodium hydroxide / tetrahydrofuran; water / 25 °C / Inert atmosphere
4: N-ethyl-N,N-diisopropylamine / dichloromethane / 10 h / 0 - 20 °C / Inert atmosphere
5: [bis(acetoxy)iodo]benzene; calcium carbonate; iodine / cyclohexane / 1.5 h / Inert atmosphere; Irradiation; Reflux
6: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
With pyridine; lithium aluminium tetrahydride; [bis(acetoxy)iodo]benzene; dimethylsulfide borane complex; dihydrogen peroxide; iodine; N-ethyl-N,N-diisopropylamine; calcium carbonate; sodium hydroxide; In tetrahydrofuran; dichloromethane; cyclohexane; water; 2: |Corey-Bakshi-Shibata Reduction / 3: |Brown Hydroboration;
3β-(toluene-4-sulfonyloxy)-pregna-5,16-dien-20-one
6996-36-7

3β-(toluene-4-sulfonyloxy)-pregna-5,16-dien-20-one

C<sub>40</sub>H<sub>55</sub>BrO<sub>5</sub>Si

C40H55BrO5Si

Conditions
Conditions Yield
Multi-step reaction with 7 steps
1: pyridine / 4 h / Inert atmosphere; Reflux
2: dimethylsulfide borane complex / tetrahydrofuran / 20 °C / Inert atmosphere; Cooling
3: dihydrogen peroxide; sodium hydroxide / tetrahydrofuran; water / 25 °C / Inert atmosphere
4: N-ethyl-N,N-diisopropylamine / dichloromethane / 10 h / 0 - 20 °C / Inert atmosphere
5: [bis(acetoxy)iodo]benzene; calcium carbonate; iodine / cyclohexane / 1.5 h / Inert atmosphere; Irradiation; Reflux
6: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
7: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 1 h / 20 °C / Inert atmosphere
With pyridine; dmap; lithium aluminium tetrahydride; [bis(acetoxy)iodo]benzene; dimethylsulfide borane complex; dihydrogen peroxide; iodine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; calcium carbonate; sodium hydroxide; In tetrahydrofuran; dichloromethane; cyclohexane; water; 2: |Corey-Bakshi-Shibata Reduction / 3: |Brown Hydroboration;
3β-(toluene-4-sulfonyloxy)-pregna-5,16-dien-20-one
6996-36-7

3β-(toluene-4-sulfonyloxy)-pregna-5,16-dien-20-one

C<sub>40</sub>H<sub>53</sub>BrO<sub>5</sub>Si

C40H53BrO5Si

Conditions
Conditions Yield
Multi-step reaction with 8 steps
1: pyridine / 4 h / Inert atmosphere; Reflux
2: dimethylsulfide borane complex / tetrahydrofuran / 20 °C / Inert atmosphere; Cooling
3: dihydrogen peroxide; sodium hydroxide / tetrahydrofuran; water / 25 °C / Inert atmosphere
4: N-ethyl-N,N-diisopropylamine / dichloromethane / 10 h / 0 - 20 °C / Inert atmosphere
5: [bis(acetoxy)iodo]benzene; calcium carbonate; iodine / cyclohexane / 1.5 h / Inert atmosphere; Irradiation; Reflux
6: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
7: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 1 h / 20 °C / Inert atmosphere
8: Dess-Martin periodane / dichloromethane / 5 h / 20 °C / Inert atmosphere
With pyridine; dmap; lithium aluminium tetrahydride; [bis(acetoxy)iodo]benzene; dimethylsulfide borane complex; dihydrogen peroxide; iodine; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; calcium carbonate; sodium hydroxide; In tetrahydrofuran; dichloromethane; cyclohexane; water; 2: |Corey-Bakshi-Shibata Reduction / 3: |Brown Hydroboration / 8: |Dess-Martin Oxidation;
3β-(toluene-4-sulfonyloxy)-pregna-5,16-dien-20-one
6996-36-7

3β-(toluene-4-sulfonyloxy)-pregna-5,16-dien-20-one

C<sub>40</sub>H<sub>54</sub>O<sub>5</sub>Si

C40H54O5Si

Conditions
Conditions Yield
Multi-step reaction with 9 steps
1: pyridine / 4 h / Inert atmosphere; Reflux
2: dimethylsulfide borane complex / tetrahydrofuran / 20 °C / Inert atmosphere; Cooling
3: dihydrogen peroxide; sodium hydroxide / tetrahydrofuran; water / 25 °C / Inert atmosphere
4: N-ethyl-N,N-diisopropylamine / dichloromethane / 10 h / 0 - 20 °C / Inert atmosphere
5: [bis(acetoxy)iodo]benzene; calcium carbonate; iodine / cyclohexane / 1.5 h / Inert atmosphere; Irradiation; Reflux
6: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
7: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 1 h / 20 °C / Inert atmosphere
8: Dess-Martin periodane / dichloromethane / 5 h / 20 °C / Inert atmosphere
9: samarium diiodide / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
With pyridine; dmap; lithium aluminium tetrahydride; samarium diiodide; [bis(acetoxy)iodo]benzene; dimethylsulfide borane complex; dihydrogen peroxide; iodine; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; calcium carbonate; sodium hydroxide; In tetrahydrofuran; dichloromethane; cyclohexane; water; 2: |Corey-Bakshi-Shibata Reduction / 3: |Brown Hydroboration / 8: |Dess-Martin Oxidation / 9: |Reformatsky Reaction;

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