constructor
New member
anybody tried this out?
SYNTHESIS OF TESTOSTERONE FROM DHEA
Testerone from bacteria culture
US Patent # 2,236,574
Suspend 40g yeast in 160 ml water and add, if
possible, 1.5g of disodium hydrogen phosphate and
potassium dihydrogen phosphate. Shake in oxygen
atmosphere for 1 day and then add lg (1000mg) DHEA
suspended in 150ml of
water and shake for another 2 days in oxygen
atmosphere. Then add 130g invert sugar (or brown sugar
or honey) and let stand 3 days at room temperature.
The mixture is then extracted with three 50ml portions
of ether (shaken with the
ether then the ether separated) or methylene chloride,
and the ether washed by shaking with water and
separating ether solution. Evaporate ether to get
testosterone.
SYNTHESIS OF ESTER OF TESTOSTERONE
(cypionate and propionate)
Dissolve 5g testosterone (or analog) in 25mi pyridine
or dry ether and add 3g propionic anhydride (or
propionyl chloride) OR cypionyl
chloride(cyclopentylpropionyl chloride) to get the
propionate and cypionate
respectively. Let stand over night and add excess
water, filter, wash, and dry.
Steroids Related to Testosterone
Oil-soluble derivatives of testosterone itself predate
those of its 19-nor congener, these agents too are
used to administer depot injections so as to provide
in effect long term blood levels of drug. Thus,
acylation of testosterone with propionyl chloride in
the presence of pyridine yields
testosterone propionate; acylation by means of
decanoic anhydride yields testosterone decanoate.
Finally, reaction with 3-cyclopentylpropionyl chloride
affords testosterone cypionate. This last undergoes
hydrolysis unusually slowly because of the presence of
two substituents at the 6 postion.
Reaction of dehydroepiandrosterone (DHEA) with an
excess of methylmagnesium bromide affords the
17a-methyl compound; again the aforementioned stedc
effects lead to high stereoselectivity. Oppenauer
oxidation of the resultant
intermediate proceeds with a shift of the double bond
into conjugation to yield methyltestosterone. When the
initial condensation is canted out with the Grignard
reagent from allyl bromide instead, this sequence
yields allylestrenol. Perhaps most startling is the
fact that the product obtained
from the use of a metal acetylide in this synthesis .
ethisterone, shows little if any, if any androgenic
potency. Instead, the compound is an orally effective
progestin.
These agents have all been used at one time as orally
active
anabolic-androgenic agents. Dehydrogenation of
methyltestosterone by means of chloranil extends the
conjugation to afford the 4,6-diene-3-one- system.
This
compound in turn undergoes 1,6 conjugate addition of
methylmagnesium bromide in the presence of cuprous
chloride to afford largely the 6a-methyl product,known
as bolasterones.
Dehydrogenation with selenium dioxide, on the other
hand, affords the cross conjugated diene, aka
Dianabol.
Hydroxylation of the double bond of methyltestosterone
by means of osmium tetro dde and hydrogen peroxide
afford the 4,5 diol. This undergoes beta elimination
on treatment with base to yield oxymestrone.
Catalytic reduction of DHEA goes as expected largely
from the unhindered side of the molecule to afford a
trans A/B dng fusion. Reaction with methyl Grignard
reagent followed by oxidation of the intermediate
yields androstanolone (1). Formylation of (1) with
ethyl formate and base gives
oxymetholone (aka Anadrol), Catalytic reduction of the
analogous hydroxmethylene compound from
dihydrotestosterone propionate gives first the
28-methyl product. Treatment with base leads this to
isomerize to the thermodynamically favored equatedal
2a-methyl compound., dromostanolone
propionate. The formyl ketone undergoes a reaction
typical of this fuctional array on treatment with
hydazine, leading to formation of the anabolic
steroidal pyrazole, stanazole.
--------------------------------------------------------------------------
SYNTHESIS OF TESTOSTERONE FROM DHEA
Testerone from bacteria culture
US Patent # 2,236,574
Suspend 40g yeast in 160 ml water and add, if
possible, 1.5g of disodium hydrogen phosphate and
potassium dihydrogen phosphate. Shake in oxygen
atmosphere for 1 day and then add lg (1000mg) DHEA
suspended in 150ml of
water and shake for another 2 days in oxygen
atmosphere. Then add 130g invert sugar (or brown sugar
or honey) and let stand 3 days at room temperature.
The mixture is then extracted with three 50ml portions
of ether (shaken with the
ether then the ether separated) or methylene chloride,
and the ether washed by shaking with water and
separating ether solution. Evaporate ether to get
testosterone.
SYNTHESIS OF ESTER OF TESTOSTERONE
(cypionate and propionate)
Dissolve 5g testosterone (or analog) in 25mi pyridine
or dry ether and add 3g propionic anhydride (or
propionyl chloride) OR cypionyl
chloride(cyclopentylpropionyl chloride) to get the
propionate and cypionate
respectively. Let stand over night and add excess
water, filter, wash, and dry.
Steroids Related to Testosterone
Oil-soluble derivatives of testosterone itself predate
those of its 19-nor congener, these agents too are
used to administer depot injections so as to provide
in effect long term blood levels of drug. Thus,
acylation of testosterone with propionyl chloride in
the presence of pyridine yields
testosterone propionate; acylation by means of
decanoic anhydride yields testosterone decanoate.
Finally, reaction with 3-cyclopentylpropionyl chloride
affords testosterone cypionate. This last undergoes
hydrolysis unusually slowly because of the presence of
two substituents at the 6 postion.
Reaction of dehydroepiandrosterone (DHEA) with an
excess of methylmagnesium bromide affords the
17a-methyl compound; again the aforementioned stedc
effects lead to high stereoselectivity. Oppenauer
oxidation of the resultant
intermediate proceeds with a shift of the double bond
into conjugation to yield methyltestosterone. When the
initial condensation is canted out with the Grignard
reagent from allyl bromide instead, this sequence
yields allylestrenol. Perhaps most startling is the
fact that the product obtained
from the use of a metal acetylide in this synthesis .
ethisterone, shows little if any, if any androgenic
potency. Instead, the compound is an orally effective
progestin.
These agents have all been used at one time as orally
active
anabolic-androgenic agents. Dehydrogenation of
methyltestosterone by means of chloranil extends the
conjugation to afford the 4,6-diene-3-one- system.
This
compound in turn undergoes 1,6 conjugate addition of
methylmagnesium bromide in the presence of cuprous
chloride to afford largely the 6a-methyl product,known
as bolasterones.
Dehydrogenation with selenium dioxide, on the other
hand, affords the cross conjugated diene, aka
Dianabol.
Hydroxylation of the double bond of methyltestosterone
by means of osmium tetro dde and hydrogen peroxide
afford the 4,5 diol. This undergoes beta elimination
on treatment with base to yield oxymestrone.
Catalytic reduction of DHEA goes as expected largely
from the unhindered side of the molecule to afford a
trans A/B dng fusion. Reaction with methyl Grignard
reagent followed by oxidation of the intermediate
yields androstanolone (1). Formylation of (1) with
ethyl formate and base gives
oxymetholone (aka Anadrol), Catalytic reduction of the
analogous hydroxmethylene compound from
dihydrotestosterone propionate gives first the
28-methyl product. Treatment with base leads this to
isomerize to the thermodynamically favored equatedal
2a-methyl compound., dromostanolone
propionate. The formyl ketone undergoes a reaction
typical of this fuctional array on treatment with
hydazine, leading to formation of the anabolic
steroidal pyrazole, stanazole.
--------------------------------------------------------------------------
Last edited:
