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15183-37-6

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  • (8r,9s,13s,14s,15r,16r,17r)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,15,16,17-tetrol

    Cas No: 15183-37-6

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  • (8r,9s,13s,14s,15r,16r,17r)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,15,16,17-tetrol

    Cas No: 15183-37-6

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15183-37-6 Usage

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 15183-37-6 differently. You can refer to the following data:
1. Estetrol is an estrogen steroid hormone exclusively produced by fetal liver from estradiol and estriol during pregnancy. It binds to estrogen receptors (ERs) with 4-fold higher affinity for ERα over ERβ and exhibits estrogenic effects in most tissues expressing ERs (bone, brain, vagina, and endometrium). In breast tumors, however, estetrol acts as an estrogen antagonist in the presence of estradiol, preventing tumor growth.
2. A metabolite of Estradiol. It is an estrogenic steroid synthesized exclusively by the fetal liver during human pregnancy and reaching the maternal circulation through the placenta.

Check Digit Verification of cas no

The CAS Registry Mumber 15183-37-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,5,1,8 and 3 respectively; the second part has 2 digits, 3 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 15183-37:
(7*1)+(6*5)+(5*1)+(4*8)+(3*3)+(2*3)+(1*7)=96
96 % 10 = 6
So 15183-37-6 is a valid CAS Registry Number.
InChI:InChI=1/C18H24O4/c1-18-7-6-12-11-5-3-10(19)8-9(11)2-4-13(12)14(18)15(20)16(21)17(18)22/h3,5,8,12-17,19-22H,2,4,6-7H2,1H3/t12?,13-,14?,15?,16?,17+,18+/m1/s1

15183-37-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name (8R,9S,13S,14S,15R,16R,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,15,16,17-tetrol

1.2 Other means of identification

Product number -
Other names ESTETROL

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:15183-37-6 SDS

15183-37-6Synthetic route

(15α,16α,17β)-3-hydroxyestra-1,3,5(10)-triene-15,16,17-triyl triacetate

(15α,16α,17β)-3-hydroxyestra-1,3,5(10)-triene-15,16,17-triyl triacetate

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
With potassium carbonate In methanol at 20 - 25℃; for 3h; Inert atmosphere;97.22%
With potassium carbonate at 25℃; for 4h;13 g
(15α,16α,17β)-3-hydroxyestra-1,3,5(10)-triene-15,16,17-triyl triformiate

(15α,16α,17β)-3-hydroxyestra-1,3,5(10)-triene-15,16,17-triyl triformiate

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
With potassium carbonate In methanol at 20 - 25℃; for 3h; Inert atmosphere;97%
15α,16α-dihydroxyestradiol 3-benzoate

15α,16α-dihydroxyestradiol 3-benzoate

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
With sodium hydroxide In methanol at 40 - 45℃; for 2h;94%
17-acetyl estetrol

17-acetyl estetrol

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
With potassium carbonate In methanol at 20℃; for 4h;92.5%
Stage #1: 17-acetyl estetrol With methanol; potassium carbonate at 20℃; for 4h;
Stage #2: With hydrogenchloride In chloroform; water
92.5%
3-benzoyloxy-17β-(1-butoxyethoxy)estra-1,3,5(10),15-tetraene

3-benzoyloxy-17β-(1-butoxyethoxy)estra-1,3,5(10),15-tetraene

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Stage #1: 3-benzoyloxy-17β-(1-butoxyethoxy)estra-1,3,5(10),15-tetraene With trimethylamine-N-oxide In tetrahydrofuran at 50 - 55℃;
Stage #2: With potassium carbonate In tetrahydrofuran; water
91.7%
Multi-step reaction with 2 steps
1: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
2: sodium hydroxide / methanol / 2 h / 40 - 45 °C
View Scheme
3,17β-O-bis(tetrahydro-2H-pyran-2-yl)-Δ-15-estradiol

3,17β-O-bis(tetrahydro-2H-pyran-2-yl)-Δ-15-estradiol

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Stage #1: 3,17β-O-bis(tetrahydro-2H-pyran-2-yl)-Δ-15-estradiol With 4-methylmorpholine N-oxide In tetrahydrofuran at 20℃;
Stage #2: With toluene-4-sulfonic acid at 40℃; pH=4;
40%
3,17β-diacetoxyestra-1,3,5(10)-triene-15α,16α-diol
16127-99-4

3,17β-diacetoxyestra-1,3,5(10)-triene-15α,16α-diol

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
With sodium hydroxide In methanol at 4℃; for 24h;21 mg
15-dehydroestradiol 3,17-diacetate
16127-98-3

15-dehydroestradiol 3,17-diacetate

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 46 percent / OsO4 / benzene; pyridine / Ambient temperature
2: 21 mg / 1 N NaOH / methanol / 24 h / 4 °C
View Scheme
Reaxys ID: 11888347

Reaxys ID: 11888347

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Estrone
53-16-7

Estrone

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: potassium carbonate / dichloromethane; methanol / 16 h / Reflux
2.1: triethylamine / dichloromethane / 1 h / 20 °C
3.1: oxygen / palladium diacetate / dichloromethane; dimethyl sulfoxide / 35 °C
4.1: cerium(III) chloride heptahydrate / tetrahydrofuran; methanol / 1 h / 20 °C
4.2: 2 h / 0 - 8 °C
5.1: pyridine / dmap / 2 h / 20 °C
6.1: trimethylamine-N-oxide / ~5percent w/w OsO4 on PVP / tetrahydrofuran / 50 °C
7.1: hydrogen / palladium 10% on activated carbon / methanol / 24 h / 20 °C / 760.05 Torr
8.1: potassium carbonate; methanol / 4 h / 20 °C
View Scheme
Multi-step reaction with 10 steps
1: triethylamine / dichloromethane / 20 - 30 °C
2: orthoformic acid triethyl ester; toluene-4-sulfonic acid / 15 h / 35 °C
3: Pyridine hydrobromide / tetrahydrofuran; ethylene glycol / 0.67 h / 20 °C
4: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
5: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
6: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
7: triethylamine / dichloromethane / 1 h / 10 - 30 °C / Inert atmosphere
8: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
9: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
10: sodium hydroxide / methanol / 2 h / 40 - 45 °C
View Scheme
Multi-step reaction with 8 steps
1.1: triethylamine / dichloromethane / 20 - 30 °C
2.1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / 15 h / 35 °C
3.1: Pyridine hydrobromide / tetrahydrofuran; ethylene glycol / 0.67 h / 20 °C
4.1: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
5.1: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
6.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
7.1: toluene-4-sulfonic acid / dichloromethane / 5 - 20 °C / Inert atmosphere; Molecular sieve
8.1: 4-methylmorpholine N-oxide / tetrahydrofuran / 20 °C
8.2: 40 °C / pH 4
View Scheme
(14α)-3-benzyloxy-1,3,5(10),15-estratetraen-17-one
138743-03-0

(14α)-3-benzyloxy-1,3,5(10),15-estratetraen-17-one

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: cerium(III) chloride heptahydrate / tetrahydrofuran; methanol / 1 h / 20 °C
1.2: 2 h / 0 - 8 °C
2.1: pyridine / dmap / 2 h / 20 °C
3.1: trimethylamine-N-oxide / ~5percent w/w OsO4 on PVP / tetrahydrofuran / 50 °C
4.1: hydrogen / palladium 10% on activated carbon / methanol / 24 h / 20 °C / 760.05 Torr
5.1: potassium carbonate; methanol / 4 h / 20 °C
View Scheme
(17β)-3-(phenylmethoxy)-estra-1,3,5(10),15-tetraen-17-ol

(17β)-3-(phenylmethoxy)-estra-1,3,5(10),15-tetraen-17-ol

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / dmap / 2 h / 20 °C
2: trimethylamine-N-oxide / ~5percent w/w OsO4 on PVP / tetrahydrofuran / 50 °C
3: hydrogen / palladium 10% on activated carbon / methanol / 24 h / 20 °C / 760.05 Torr
4: potassium carbonate; methanol / 4 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; tert-butyl alcohol; water / 24 h / 20 - 25 °C / Inert atmosphere
2: acetic anhydride; pyridine / 1.42 h / 0 - 10 °C
3: palladium 10% on activated carbon; hydrogen / ethyl acetate / 4 h / 20 - 25 °C / 760.05 Torr
4: potassium carbonate / methanol / 3 h / 20 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; tert-butyl alcohol; water / 24 h / 20 - 25 °C / Inert atmosphere
2: triethylamine; dmap / dichloromethane / 2 h / Inert atmosphere
3: palladium 10% on activated carbon; hydrogen / ethyl acetate / 3 h / 20 - 25 °C / 760.05 Torr
4: potassium carbonate / methanol / 3 h / 20 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1: osmium(VIII) oxide; trimethylamine-N-oxide / tetrahydrofuran / 16 h / 50 °C / Inert atmosphere
2: dmap / pyridine / 4 h / 25 °C
3: palladium 10% on activated carbon; hydrogen / methanol / 22 h / 45 °C / 2250.23 Torr
4: potassium carbonate / 4 h / 25 °C
View Scheme
17β-acetyloxy-3-benzyloxy-estra-1,3,5(10),15-tetraene

17β-acetyloxy-3-benzyloxy-estra-1,3,5(10),15-tetraene

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: trimethylamine-N-oxide / ~5percent w/w OsO4 on PVP / tetrahydrofuran / 50 °C
2: hydrogen / palladium 10% on activated carbon / methanol / 24 h / 20 °C / 760.05 Torr
3: potassium carbonate; methanol / 4 h / 20 °C
View Scheme
3-benzyloxyestra-1,3,5(10)-trien-17-one
858-98-0

3-benzyloxyestra-1,3,5(10)-trien-17-one

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: triethylamine / dichloromethane / 1 h / 20 °C
2.1: oxygen / palladium diacetate / dichloromethane; dimethyl sulfoxide / 35 °C
3.1: cerium(III) chloride heptahydrate / tetrahydrofuran; methanol / 1 h / 20 °C
3.2: 2 h / 0 - 8 °C
4.1: pyridine / dmap / 2 h / 20 °C
5.1: trimethylamine-N-oxide / ~5percent w/w OsO4 on PVP / tetrahydrofuran / 50 °C
6.1: hydrogen / palladium 10% on activated carbon / methanol / 24 h / 20 °C / 760.05 Torr
7.1: potassium carbonate; methanol / 4 h / 20 °C
View Scheme
3-benzyloxy-17-trimethylsilyloxy-estra-1,3,5(10),16-tetraene
213819-19-3

3-benzyloxy-17-trimethylsilyloxy-estra-1,3,5(10),16-tetraene

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: oxygen / palladium diacetate / dichloromethane; dimethyl sulfoxide / 35 °C
2.1: cerium(III) chloride heptahydrate / tetrahydrofuran; methanol / 1 h / 20 °C
2.2: 2 h / 0 - 8 °C
3.1: pyridine / dmap / 2 h / 20 °C
4.1: trimethylamine-N-oxide / ~5percent w/w OsO4 on PVP / tetrahydrofuran / 50 °C
5.1: hydrogen / palladium 10% on activated carbon / methanol / 24 h / 20 °C / 760.05 Torr
6.1: potassium carbonate; methanol / 4 h / 20 °C
View Scheme
3,17β-O-bis(methoxymethyl)-Δ-15-estradiol

3,17β-O-bis(methoxymethyl)-Δ-15-estradiol

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Stage #1: 3,17β-O-bis(methoxymethyl)-Δ-15-estradiol With trimethylamine-N-oxide In tetrahydrofuran at 50 - 55℃;
Stage #2: With acetic acid In tetrahydrofuran; water Reagent/catalyst;
0.26 g
estrone 3-benzoate
2393-53-5

estrone 3-benzoate

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / 15 h / 35 °C
2.1: Pyridine hydrobromide / tetrahydrofuran; ethylene glycol / 0.67 h / 20 °C
3.1: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
4.1: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
5.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
6.1: toluene-4-sulfonic acid / dichloromethane / 5 - 20 °C / Inert atmosphere; Molecular sieve
7.1: 4-methylmorpholine N-oxide / tetrahydrofuran / 20 °C
7.2: 40 °C / pH 4
View Scheme
Multi-step reaction with 7 steps
1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / 15 h / 35 °C
2: Pyridine hydrobromide / tetrahydrofuran; ethylene glycol / 0.67 h / 20 °C
3: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
4: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
5: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
6: toluene-4-sulfonic acid; lithium bromide / tetrahydrofuran / 20 °C / Inert atmosphere
7: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 7 steps
1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / 15 h / 35 °C
2: Pyridine hydrobromide / tetrahydrofuran; ethylene glycol / 0.67 h / 20 °C
3: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
4: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
5: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
6: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
7: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 8 steps
1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / 15 h / 35 °C
2: Pyridine hydrobromide / tetrahydrofuran; ethylene glycol / 0.67 h / 20 °C
3: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
4: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
5: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
6: triethylamine / dichloromethane / 1 h / 10 - 30 °C / Inert atmosphere
7: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
8: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 9 steps
1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / 15 h / 35 °C
2: Pyridine hydrobromide / tetrahydrofuran; ethylene glycol / 0.67 h / 20 °C
3: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
4: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
5: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
6: triethylamine / dichloromethane / 1 h / 10 - 30 °C / Inert atmosphere
7: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
8: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
9: sodium hydroxide / methanol / 2 h / 40 - 45 °C
View Scheme
17,17-ethylenedioxyestrone 3-benzoate

17,17-ethylenedioxyestrone 3-benzoate

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: Pyridine hydrobromide / tetrahydrofuran; ethylene glycol / 0.67 h / 20 °C
2.1: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
3.1: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
4.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
5.1: toluene-4-sulfonic acid / dichloromethane / 5 - 20 °C / Inert atmosphere; Molecular sieve
6.1: 4-methylmorpholine N-oxide / tetrahydrofuran / 20 °C
6.2: 40 °C / pH 4
View Scheme
Multi-step reaction with 6 steps
1: Pyridine hydrobromide / tetrahydrofuran; ethylene glycol / 0.67 h / 20 °C
2: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
3: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
4: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
5: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
6: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 6 steps
1: Pyridine hydrobromide / tetrahydrofuran; ethylene glycol / 0.67 h / 20 °C
2: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
3: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
4: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
5: toluene-4-sulfonic acid; lithium bromide / tetrahydrofuran / 20 °C / Inert atmosphere
6: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 7 steps
1: Pyridine hydrobromide / tetrahydrofuran; ethylene glycol / 0.67 h / 20 °C
2: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
3: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
4: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
5: triethylamine / dichloromethane / 1 h / 10 - 30 °C / Inert atmosphere
6: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
7: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 8 steps
1: Pyridine hydrobromide / tetrahydrofuran; ethylene glycol / 0.67 h / 20 °C
2: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
3: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
4: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
5: triethylamine / dichloromethane / 1 h / 10 - 30 °C / Inert atmosphere
6: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
7: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
8: sodium hydroxide / methanol / 2 h / 40 - 45 °C
View Scheme
3-benzoyloxy-16-bromo-17,17-(ethylenedioxy)estra-1,3,5(10)-triene

3-benzoyloxy-16-bromo-17,17-(ethylenedioxy)estra-1,3,5(10)-triene

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
2.1: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
3.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
4.1: toluene-4-sulfonic acid / dichloromethane / 5 - 20 °C / Inert atmosphere; Molecular sieve
5.1: 4-methylmorpholine N-oxide / tetrahydrofuran / 20 °C
5.2: 40 °C / pH 4
View Scheme
Multi-step reaction with 5 steps
1: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
2: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
3: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
4: toluene-4-sulfonic acid; lithium bromide / tetrahydrofuran / 20 °C / Inert atmosphere
5: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 5 steps
1: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
2: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
3: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
4: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
5: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 6 steps
1: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
2: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
3: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
4: triethylamine / dichloromethane / 1 h / 10 - 30 °C / Inert atmosphere
5: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
6: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 7 steps
1: potassium tert-butylate / dimethyl sulfoxide / 20 h / 40 - 45 °C
2: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
3: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
4: triethylamine / dichloromethane / 1 h / 10 - 30 °C / Inert atmosphere
5: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
6: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
7: sodium hydroxide / methanol / 2 h / 40 - 45 °C
View Scheme
17,17-ethylenedioxy-3-hydroxyestra-1,3,5(10),15-tetraene

17,17-ethylenedioxy-3-hydroxyestra-1,3,5(10),15-tetraene

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
2: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
3: toluene-4-sulfonic acid; lithium bromide / tetrahydrofuran / 20 °C / Inert atmosphere
4: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 4 steps
1: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
2: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
4: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 5 steps
1: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
2: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
3: triethylamine / dichloromethane / 1 h / 10 - 30 °C / Inert atmosphere
4: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
5: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 6 steps
1: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
2: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
3: triethylamine / dichloromethane / 1 h / 10 - 30 °C / Inert atmosphere
4: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
5: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
6: sodium hydroxide / methanol / 2 h / 40 - 45 °C
View Scheme
Multi-step reaction with 4 steps
1.1: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
2.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
3.1: toluene-4-sulfonic acid / dichloromethane / 5 - 20 °C / Inert atmosphere; Molecular sieve
4.1: 4-methylmorpholine N-oxide / tetrahydrofuran / 20 °C
4.2: 40 °C / pH 4
View Scheme
3-hydroxyestra-1,3,5(10),15-tetraen-17-one
3563-25-5

3-hydroxyestra-1,3,5(10),15-tetraen-17-one

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
3: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 3 steps
1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
2: toluene-4-sulfonic acid; lithium bromide / tetrahydrofuran / 20 °C / Inert atmosphere
3: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 4 steps
1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
2: triethylamine / dichloromethane / 1 h / 10 - 30 °C / Inert atmosphere
3: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
4: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 5 steps
1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
2: triethylamine / dichloromethane / 1 h / 10 - 30 °C / Inert atmosphere
3: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
4: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
5: sodium hydroxide / methanol / 2 h / 40 - 45 °C
View Scheme
Multi-step reaction with 3 steps
1.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 - 5 °C
2.1: toluene-4-sulfonic acid / dichloromethane / 5 - 20 °C / Inert atmosphere; Molecular sieve
3.1: 4-methylmorpholine N-oxide / tetrahydrofuran / 20 °C
3.2: 40 °C / pH 4
View Scheme
Δ-15-estradiol 3-benzoate

Δ-15-estradiol 3-benzoate

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
2: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 3 steps
1: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
2: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
3: sodium hydroxide / methanol / 2 h / 40 - 45 °C
View Scheme
estra-1,3,5(10),15-tetraene-3,17β-diol
58699-14-2

estra-1,3,5(10),15-tetraene-3,17β-diol

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene-4-sulfonic acid; lithium bromide / tetrahydrofuran / 20 °C / Inert atmosphere
2: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
2: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 1 h / 10 - 30 °C / Inert atmosphere
2: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
3: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
View Scheme
Multi-step reaction with 4 steps
1: triethylamine / dichloromethane / 1 h / 10 - 30 °C / Inert atmosphere
2: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C / Molecular sieve; Inert atmosphere
3: trimethylamine-N-oxide / tetrahydrofuran / 50 - 55 °C
4: sodium hydroxide / methanol / 2 h / 40 - 45 °C
View Scheme
Multi-step reaction with 2 steps
1.1: toluene-4-sulfonic acid / dichloromethane / 5 - 20 °C / Inert atmosphere; Molecular sieve
2.1: 4-methylmorpholine N-oxide / tetrahydrofuran / 20 °C
2.2: 40 °C / pH 4
View Scheme
(17β)-3-(phenylmethoxy)-estra-1,3,5(10)-triene-15,16,17-triol

(17β)-3-(phenylmethoxy)-estra-1,3,5(10)-triene-15,16,17-triol

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine; dmap / ethyl acetate / 3 h / 35 - 40 °C / Inert atmosphere
2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 3 h / 20 - 25 °C / 760.05 Torr
3: potassium carbonate / methanol / 3 h / 20 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: dmap / pyridine / 4 h / 25 °C
2: palladium 10% on activated carbon; hydrogen / methanol / 22 h / 45 °C / 2250.23 Torr
3: potassium carbonate / 4 h / 25 °C
View Scheme
(15α,16α,17β)-3-(benzyloxy)estra-1,3,5(10)-triene-15,16,17-triyl triacetate

(15α,16α,17β)-3-(benzyloxy)estra-1,3,5(10)-triene-15,16,17-triyl triacetate

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 3 h / 20 - 25 °C / 760.05 Torr
2: potassium carbonate / methanol / 3 h / 20 - 25 °C / Inert atmosphere
View Scheme
(15α,16α,17β)-3-(benzyloxy)estra-1,3,5(10)-triene-15,16,17-triol

(15α,16α,17β)-3-(benzyloxy)estra-1,3,5(10)-triene-15,16,17-triol

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine; dmap / dichloromethane / 2 h / Inert atmosphere
2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 3 h / 20 - 25 °C / 760.05 Torr
3: potassium carbonate / methanol / 3 h / 20 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: acetic anhydride; pyridine / 1.42 h / 0 - 10 °C
2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 4 h / 20 - 25 °C / 760.05 Torr
3: potassium carbonate / methanol / 3 h / 20 - 25 °C / Inert atmosphere
View Scheme
4-bromoethylbutanoate
2969-81-5

4-bromoethylbutanoate

15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

4-O-[15α,16α,17β-trihydroxyestra-1,3,5(10)-trien-3-yl]butanoic acid ethyl ester

4-O-[15α,16α,17β-trihydroxyestra-1,3,5(10)-trien-3-yl]butanoic acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 80℃; for 1h; Alkylation;206 mg
15α-hydroxyestriol
15183-37-6

15α-hydroxyestriol

4-O-[15α,16α,17β-trihydroxyestra-1,3,5(10)-trien-3-yl]butanoic acid

4-O-[15α,16α,17β-trihydroxyestra-1,3,5(10)-trien-3-yl]butanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 206 mg / K2CO3 / dimethylsulfoxide / 1 h / 80 °C
2: 151 mg / 5 N aq. NaOH / methanol / 14 h / 4 °C
View Scheme

15183-37-6Downstream Products

15183-37-6Related news

Ovulation inhibition by ESTETROL (cas 15183-37-6) in an in vivo model08/05/2019

BackgroundCurrently, the synthetic steroid ethinylestradiol (EE) is the preferred estrogen in combined oral contraceptives. The aim of the present study was to evaluate the effectiveness of the natural steroid estetrol (E4) as an ovulation inhibitor in rats when compared to EE.detailed

Whole blood microsampling for the quantitation of ESTETROL (cas 15183-37-6) without derivatization by liquid chromatography-tandem mass spectrometry08/04/2019

Quantitative bioanalysis and especially pharmacokinetic studies are challenging since only low volumes of biological material are available and low concentrations (ng/ml) are often expected. In this context, volumetric absorptive microsampling (VAMS) devices were developed to accurately collect ...detailed

Reduced hemostatic effects with drospirenone-based oral contraceptives containing ESTETROL (cas 15183-37-6) vs. ethinyl estradiol08/03/2019

SummaryObjectiveThe effects of estetrol (E4), a natural fetal estrogen, combined with drospirenone (DRSP) were evaluated on plasma levels of sex hormone-binding globulin (SHBG), angiotensinogen and 12 hemostasis markers.detailed

Effect of ESTETROL (cas 15183-37-6) on Beta-Endorphin level in female rats08/02/2019

IntroductionEstetrol (E4), a naturally occurring estrogen produced exclusively by human fetal liver, is currently being evaluated for potential use in contraception and menopausal care in humans. The present study was designed to profile E4 effects on the central nervous system, to assess the in...detailed

Effect of ESTETROL (cas 15183-37-6) administration on brain and serum allopregnanolone in intact and ovariectomized rats08/01/2019

IntroductionEstetrol (E4), a naturally occurring estrogen only produced by the human fetal liver, is being evaluated in human studies for potential use in contraception and menopausal care. The present study was designed to profile E4 in the central nervous system, to assess the in vivo effects ...detailed

Development of injectable liposomes and drug-in-cyclodextrin-in-liposome formulations encapsulating ESTETROL (cas 15183-37-6) to prevent cerebral ischemia of premature babies07/31/2019

Neonatal Hypoxic-Ischemic Encephalopathy (HIE), a brain disease due to brain hypoxia along with ischemia and reduced cerebral blood flow, is one of the primary reasons of severe injury among babies prematurely born. No efficacy treatment is available to the present day. Estetrol (E4), a major es...detailed

Clinical effects of the fetal estrogen ESTETROL (cas 15183-37-6) in a multiple-rising-dose study in postmenopausal women07/28/2019

ObjectiveEstetrol (E4) is a natural fetal estrogen. The safety of increasing doses of E4 and its preliminary effects on the vagina, endometrium and menopausal vasomotor symptoms were investigated.detailed

Regulatory effects of ESTETROL (cas 15183-37-6) on the endothelial plasminogen pathway and endothelial cell migration07/27/2019

BackgroundEstetrol (E4) is a natural estrogen produced solely during human pregnancy. E4 is suitable for clinical use since it acts as a selective estrogen receptor modulator. In clinical trials E4 has been seen to have little or no effect on coagulation. Hence, it is interesting to investigate ...detailed

15183-37-6Relevant articles and documents

Synthesis of 15α-hydroxyestrogen 15-N-acetylglucosaminides

Suzuki, Emako,Namba, Susumu,Kurihara, Hiroyuki,Goto, Junichi,Matsuki, Yasuhiko,Nambara, Toshio

, p. 277 - 284 (1995)

The synthesis of 15-N-acetylglucosaminides of 15α-hydroxyestrone, 15α-hydroxyestradiol, and 15α-hydroxyestriol (estetrol) is described.The latter two were prepared by condensation of 2-acetamido-1α-chloro-1,2-dideoxy-3,4,6-tri-O-acetyl-D-glucopyranose with appropriately protected 15α-hydroxyestrogens by the Koenigs-Knorr reaction employing cadmium carbonate as a catalyst.Subsequent removal of protecting groups with methanolic potassium hydroxide provided the desired conjugates. 15α-Hydroxyestrone 15-N-acetylglucosaminide was synthesized from the corresponding 15α-hydroxyestradiol derivative by Jones oxidation followed by brief alkaline hydrolysis.These conjugates underwent enzymatic hydrolysis with β-N-acetylglucosaminidase from Jack beans to produce 15α-hydroxyestrogens. - Keywords: 15α-hydroxyestrogen; N-acetylglucosaminide; Koenigs-Knorr reaction; 15-methoxyestrogen; β-N-acetylglucosaminidase

PROCESS FOR PREPARING (15ΑLPHA,16ΑLPHA,17ΒETA)-ESTRA-1,3,5(10)-TRIENE-3,15,16,17-TETROL (ESTETROL) AND INTERMEDIATES OF SAID PROCESS

-

Page/Page column 14-15, (2021/04/02)

The present invention relates to a process for preparing (15α,16α,17β)-Estra-1,3,5(10)-triene-3,15,16,17-tetrol, also known as Estetrol, having the formula shown below: (I)

Process for the preparation of estetrol

-

, (2011/11/12)

The present invention relates to a process for the preparation of estra-1,3,5(10)-trien-3,15α,16α,17β-tetraol (estetrol), via a silyl enol ether derivative 17-B-oxy-3-A-oxy-estra-1,3,5(10),16-tetraene, wherein A is a protecting group and B is ―Si(R2)3. The invention further relates to a process for the synthesis of 3-A-oxy-estra-1,3,5(10),15-tetraen-17-one, wherein A is a protecting group, via said silyl enol ether derivative.

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