Benzoic acid (1S,4R)-4-((3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1-[(R)-1-hydroxy-1-methyl-2-(toluene-4-sulfonyloxy)-ethyl]-pentyl ester

Base Information

• Chemical Name: Benzoic acid (1S,4R)-4-((3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1-[(R)-1-hydroxy-1-methyl-2-(toluene-4-sulfonyloxy)-ethyl]-pentyl ester
• CAS No.: 88099-55-2
• Molecular Formula: C₄₁H₅₆O₇S
• Molecular Weight: 692.957

Synonyms:Benzoic acid (1S,4R)-4-((3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1-[(R)-1-hydroxy-1-methyl-2-(toluene-4-sulfonyloxy)-ethyl]-pentyl ester

Chemical Property of Benzoic acid (1S,4R)-4-((3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1-[(R)-1-hydroxy-1-methyl-2-(toluene-4-sulfonyloxy)-ethyl]-pentyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of Benzoic acid (1S,4R)-4-((3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1-[(R)-1-hydroxy-1-methyl-2-(toluene-4-sulfonyloxy)-ethyl]-pentyl ester

There total 24 articles about Benzoic acid (1S,4R)-4-((3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1-[(R)-1-hydroxy-1-methyl-2-(toluene-4-sulfonyloxy)-ethyl]-pentyl ester 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:

3β-hydroxy-5-cholenoic acid (5255-17-4) → Benzoic acid (1R,4R)-4-((3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1-[(S)-1-hydroxy-1-methyl-2-(toluene-4-sulfonyloxy)-ethyl]-pentyl ester (88099-55-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) toluene-p-sulphonic acid, 2.) lithium aluminium hydride / 1.) benzene, room temperature, 2 h, 2.) THF, room temperature, 1 h

2: 3.26 g / pyridinium chlorochromate / CH₂Cl₂ / 3 h / Ambient temperature

3: 1.4 g / tetrahydrofuran / 3 h / Ambient temperature

4: 115.4 mg / pyridinium dichromate / CH₂Cl₂; dimethylformamide / 2 h / Ambient temperature

5: 36.4 mg / lithium aluminium hydride, ethanol, (R)-(+)-2,2'-dihydroxy-1,1'-binaphthyl / tetrahydrofuran / 20 h / -90 °C

6: 47.8 mg / t-butyl hydroperoxide, VO(acac)2 / benzene / 3 h / Ambient temperature

7: 21 mg / potassium carbonate / propan-2-ol / 2 h / Heating

8: 155 mg / pyridine / 4 h / Ambient temperature

9: 41 mg / 70percent aq. perchloric acid / tetrahydrofuran; H₂O / 48 h / Ambient temperature

10: 162 percent / pyridine / 24 h / Ambient temperature

With pyridine; tert.-butylhydroperoxide; lithium aluminium tetrahydride; dipyridinium dichromate; perchloric acid; bis(acetylacetonate)oxovanadium; ethanol; (R)-1,1'-Bi-2-naphthol; potassium carbonate; toluene-4-sulfonic acid; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; benzene;

Reference yield:

3β-hydroxy-5-cholenoic acid (5255-17-4) → Benzoic acid (1S,4R)-4-((3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1-[(R)-1-hydroxy-1-methyl-2-(toluene-4-sulfonyloxy)-ethyl]-pentyl ester (88099-55-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) toluene-p-sulphonic acid, 2.) lithium aluminium hydride / 1.) benzene, room temperature, 2 h, 2.) THF, room temperature, 1 h

2: 3.26 g / pyridinium chlorochromate / CH₂Cl₂ / 3 h / Ambient temperature

3: 1.4 g / tetrahydrofuran / 3 h / Ambient temperature

4: 115.4 mg / pyridinium dichromate / CH₂Cl₂; dimethylformamide / 2 h / Ambient temperature

5: 35.8 mg / lithium aluminium hydride, ethanol, (S)-(-)-2,2'-dihydroxy-1,1'-binaphthyl / tetrahydrofuran / -90 °C

6: 49.2 mg / t-butyl hydroperoxide, VO(acac)2 / benzene / Ambient temperature

7: 17 mg / potassium carbonate / propan-2-ol / Heating

8: 180 mg / pyridine / Ambient temperature

9: 49 mg / 70percent aq. perchloric acid / tetrahydrofuran; H₂O / Ambient temperature

10: pyridine / Ambient temperature

With pyridine; tert.-butylhydroperoxide; lithium aluminium tetrahydride; dipyridinium dichromate; perchloric acid; bis(acetylacetonate)oxovanadium; ethanol; (S)-[1,1']-binaphthalenyl-2,2'-diol; potassium carbonate; toluene-4-sulfonic acid; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; benzene;

Reference yield:

3β-(tetrahydro-2H-pyran-2-yloxy)chol-5-en-24-ol (66414-43-5) → Benzoic acid (1S,4R)-4-((3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1-[(R)-1-hydroxy-1-methyl-2-(toluene-4-sulfonyloxy)-ethyl]-pentyl ester (88099-55-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 3.26 g / pyridinium chlorochromate / CH₂Cl₂ / 3 h / Ambient temperature

2: 1.4 g / tetrahydrofuran / 3 h / Ambient temperature

3: 115.4 mg / pyridinium dichromate / CH₂Cl₂; dimethylformamide / 2 h / Ambient temperature

4: 35.8 mg / lithium aluminium hydride, ethanol, (S)-(-)-2,2'-dihydroxy-1,1'-binaphthyl / tetrahydrofuran / -90 °C

5: 49.2 mg / t-butyl hydroperoxide, VO(acac)2 / benzene / Ambient temperature

6: 17 mg / potassium carbonate / propan-2-ol / Heating

7: 180 mg / pyridine / Ambient temperature

8: 49 mg / 70percent aq. perchloric acid / tetrahydrofuran; H₂O / Ambient temperature

9: pyridine / Ambient temperature

With pyridine; tert.-butylhydroperoxide; lithium aluminium tetrahydride; dipyridinium dichromate; perchloric acid; bis(acetylacetonate)oxovanadium; ethanol; (S)-[1,1']-binaphthalenyl-2,2'-diol; potassium carbonate; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; benzene;

upstream raw materials:

(24S,25R)-24-benzoyloxy-3β,25,26-trihydroxycholest-5-ene

p-toluenesulfonyl chloride

3β-hydroxy-5-cholenoic acid

3β-(tetrahydro-2H-pyran-2-yloxy)chol-5-en-24-ol

Downstream raw materials:

(24S)-24,25-dihydroxyvitamin D₃

C₄₁H₅₄O₅

(24S)-3β,24-dibenzoyloxy-25-trimethylsilyloxycholest-5-ene

(24R)-24,25-dihydroxyvitamin D₃

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