(17S,22R)-14,17,20,22-Tetrahydroxy-1-oxoergosta-2,5,24-trien-26-oic acid δ-lactone

Base Information

Chemical Name:(17S,22R)-14,17,20,22-Tetrahydroxy-1-oxoergosta-2,5,24-trien-26-oic acid δ-lactone
CAS No.:63115-49-1
Molecular Formula:C28H38O6
Molecular Weight:470.6
Hs Code.:

Synonyms:coagulin C;(R)-6-[(S)-1-((8R,9S,10R,13S,14R,17S)-14,17-Dihydroxy-10,13-dimethyl-1-oxo-4,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1-hydroxy-ethyl]-3,4-dimethyl-5,6-dihydro-pyran-2-one;

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (17S,22R)-14,17,20,22-Tetrahydroxy-1-oxoergosta-2,5,24-trien-26-oic acid δ-lactone

Chemical Property:

PSA：104.06000
LogP:3.54320

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of (17S,22R)-14,17,20,22-Tetrahydroxy-1-oxoergosta-2,5,24-trien-26-oic acid δ-lactone

There total 19 articles about (17S,22R)-14,17,20,22-Tetrahydroxy-1-oxoergosta-2,5,24-trien-26-oic acid δ-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:

: 114028-19-2
1α,3α-diacetoxyandrost-5-ene-17-one

: 63115-49-1
(17α,22R)-14,17,20-Trihydroxy-22,26-epoxyergosta-3,5,24-triene-1,26-dione

Guidance literature:: Multi-step reaction with 18 steps

1: (TMS)2NH, Et₃N / 1,2-dichloro-ethane / 0.75 h / -23 °C

2: 1.) Pd(OAc)2, K₂CO₃, 2.) p-toluenesulfonic acid / 1.) CH₃CN, 12 h, 2.) reflux

3: 1.) tetrabutylammonium periodate / 1.) CH₂Cl₂, 2.) 0 deg C, 20 min

4: 1.) H₂, 2.) aq. CuCl₂ / 1.) 5percent Pd-BaSO₄ / 1.) EtOH, 3 h, 2.) THF, 4 h

5: 100 percent / 5percent KOH / methanol / 2 h / Heating

7: tetrahydrofuran

8: i-Pr₂NEt / dioxane / 24 h / 80 °C

9: osmium tetraoxide, pyridine

10: 89 percent / TFAA, DMSO, Et₃N / CH₂Cl₂ / 1.5 h / -78 °C

11: 97 percent / tetrahydrofuran / 1 h / -78 °C

12: 65 percent / i-Pr₂NEt / dioxane / 24 h / 90 °C

13: 1.) O₃, 2.) Me₂S / 1.) MeOH, -100 deg C, 2.) 30 min

14: 1.) LDA / 1.) THF, HMPA, 2.) from -78 deg C to RT, 1.5 h

15: 2 M aq. H₂SO₄ / dioxane / 36 h

16: 72 percent / DMAP, pyridine / 15 h

17: 78 percent / oxidation

18: 1,5-diazabicyclo<4.3.0>non-5-ene / CH₂Cl₂ / 0.67 h

With pyridine; dmap; palladium diacetate; potassium hydroxide; osmium(VIII) oxide; dimethylsulfide; sulfuric acid; DBN; hydrogen; potassium carbonate; tetrabutylammonium periodite; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic anhydride; copper dichloride; lithium diisopropyl amide; palladium on barium sulfate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; 1,2-dichloro-ethane;
DOI:10.1021/ja00003a058

Reference yield:

: Acetic acid (1S,3R,8R,9S,10R,13S,14S)-3-acetoxy-10,13-dimethyl-17-trimethylsilanyloxy-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-1-yl ester

: 63115-49-1
(17α,22R)-14,17,20-Trihydroxy-22,26-epoxyergosta-3,5,24-triene-1,26-dione

Guidance literature:: Multi-step reaction with 17 steps

1: 1.) Pd(OAc)2, K₂CO₃, 2.) p-toluenesulfonic acid / 1.) CH₃CN, 12 h, 2.) reflux

2: 1.) tetrabutylammonium periodate / 1.) CH₂Cl₂, 2.) 0 deg C, 20 min

3: 1.) H₂, 2.) aq. CuCl₂ / 1.) 5percent Pd-BaSO₄ / 1.) EtOH, 3 h, 2.) THF, 4 h

4: 100 percent / 5percent KOH / methanol / 2 h / Heating

6: tetrahydrofuran

7: i-Pr₂NEt / dioxane / 24 h / 80 °C

8: osmium tetraoxide, pyridine

9: 89 percent / TFAA, DMSO, Et₃N / CH₂Cl₂ / 1.5 h / -78 °C

10: 97 percent / tetrahydrofuran / 1 h / -78 °C

11: 65 percent / i-Pr₂NEt / dioxane / 24 h / 90 °C

12: 1.) O₃, 2.) Me₂S / 1.) MeOH, -100 deg C, 2.) 30 min

13: 1.) LDA / 1.) THF, HMPA, 2.) from -78 deg C to RT, 1.5 h

14: 2 M aq. H₂SO₄ / dioxane / 36 h

15: 72 percent / DMAP, pyridine / 15 h

16: 78 percent / oxidation

17: 1,5-diazabicyclo<4.3.0>non-5-ene / CH₂Cl₂ / 0.67 h

With pyridine; dmap; palladium diacetate; potassium hydroxide; osmium(VIII) oxide; dimethylsulfide; sulfuric acid; DBN; hydrogen; potassium carbonate; tetrabutylammonium periodite; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; copper dichloride; lithium diisopropyl amide; palladium on barium sulfate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;
DOI:10.1021/ja00003a058

Reference yield:

: 131759-39-2
Acetic acid (1S,3R,8R,9S,10R,13S)-3,17-diacetoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13-decahydro-1H-cyclopenta[a]phenanthren-1-yl ester

: 63115-49-1
(17α,22R)-14,17,20-Trihydroxy-22,26-epoxyergosta-3,5,24-triene-1,26-dione

Guidance literature:: Multi-step reaction with 16 steps

1: 1.) tetrabutylammonium periodate / 1.) CH₂Cl₂, 2.) 0 deg C, 20 min

2: 1.) H₂, 2.) aq. CuCl₂ / 1.) 5percent Pd-BaSO₄ / 1.) EtOH, 3 h, 2.) THF, 4 h

3: 100 percent / 5percent KOH / methanol / 2 h / Heating

5: tetrahydrofuran

6: i-Pr₂NEt / dioxane / 24 h / 80 °C

7: osmium tetraoxide, pyridine

8: 89 percent / TFAA, DMSO, Et₃N / CH₂Cl₂ / 1.5 h / -78 °C

9: 97 percent / tetrahydrofuran / 1 h / -78 °C

10: 65 percent / i-Pr₂NEt / dioxane / 24 h / 90 °C

11: 1.) O₃, 2.) Me₂S / 1.) MeOH, -100 deg C, 2.) 30 min

12: 1.) LDA / 1.) THF, HMPA, 2.) from -78 deg C to RT, 1.5 h

13: 2 M aq. H₂SO₄ / dioxane / 36 h

14: 72 percent / DMAP, pyridine / 15 h

15: 78 percent / oxidation

16: 1,5-diazabicyclo<4.3.0>non-5-ene / CH₂Cl₂ / 0.67 h

With pyridine; dmap; potassium hydroxide; osmium(VIII) oxide; dimethylsulfide; sulfuric acid; DBN; hydrogen; tetrabutylammonium periodite; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; copper dichloride; lithium diisopropyl amide; palladium on barium sulfate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;
DOI:10.1021/ja00003a058