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35700-23-3

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35700-23-3 Usage

Description

15(S)-15-methyl PGF2α is a metabolically stable analog of PGF2α. It is a potent uterine stimulant and abortifacient which can be administered intramuscularly to induce labor. It induces luteolysis and reduces serum progesterone concentrations when given as an intramuscular injection in non-pregnant rhesus monkeys.

Uses

Different sources of media describe the Uses of 35700-23-3 differently. You can refer to the following data:
1. Analog of prostaglandin F2α. Oxytocic.
2. Analog of prostaglandin F2a. Oxytocic

Definition

ChEBI: Prostaglandin F2alpha in which the hydrogen at position 15 is substituted by methyl (S configuration). It is used as an abortifacient agent that is effective in both the first and second trimesters of regnancy.

Brand name

Hemabate (Pharmacia & Upjohn).

Check Digit Verification of cas no

The CAS Registry Mumber 35700-23-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,5,7,0 and 0 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 35700-23:
(7*3)+(6*5)+(5*7)+(4*0)+(3*0)+(2*2)+(1*3)=93
93 % 10 = 3
So 35700-23-3 is a valid CAS Registry Number.
InChI:InChI=1/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17?,18-,19+/m0/s1

35700-23-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name carboprost

1.2 Other means of identification

Product number -
Other names methyldinoprost

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:35700-23-3 SDS

35700-23-3Synthetic route

U 36384
35700-21-1

U 36384

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
With water; sodium hydroxide In methanol98%
C27H50O5Si

C27H50O5Si

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2h;85%
C30H56O5Si

C30H56O5Si

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2h;85%
C24H44O5Si

C24H44O5Si

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 2h;85%
C27H50O5Si

C27H50O5Si

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2h;85%
C23H40O6

C23H40O6

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
With hydrogenchloride In water; isopropyl alcohol at 55℃; for 10h;85%
C25H44O6

C25H44O6

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
With hydrogenchloride In water; isopropyl alcohol at 55℃; for 10h;85%
C37H54O5Si

C37H54O5Si

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 5h;84%
(4-carboxybutyl)triphenylphosphonium bromide
17814-85-6

(4-carboxybutyl)triphenylphosphonium bromide

C16H28O4

C16H28O4

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at -10 - -5℃; for 12.1667h; Inert atmosphere;77%
(15S)-15-methyl-PGF2α 1,11-lactone 9,15-bis(tert-butyldimethylsilyl ether)
85720-21-4

(15S)-15-methyl-PGF2α 1,11-lactone 9,15-bis(tert-butyldimethylsilyl ether)

A

Carboprost
35700-23-3

Carboprost

B

(15S)-15-methyl-PGF2α 1,11-lactone
80029-28-3

(15S)-15-methyl-PGF2α 1,11-lactone

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In 1,2-dimethoxyethane for 16h; Heating;A 42%
B 46%
(15S)-15-methyl prostaglandin F2α methyl ester
96744-82-0

(15S)-15-methyl prostaglandin F2α methyl ester

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 81 percent / pyridine / 1.) 0 deg C, 5 h, 2.) 25 deg C, 18 h
2: 60 percent / imidazole / dimethylformamide / 16 h / 80 °C
3: 89 percent / Zn, CH3OH / 1.25 h / Heating
4: 1.) 2 N aq. KOH, 2.) Ph3P / 1.) THF, CH3OH, 25 deg C, 4 h, 2.) xylene, 25 deg C, 90 min
5: xylene / 36 h / Heating
6: 42 percent / Bu4NF / 1,2-dimethoxy-ethane / 16 h / Heating
View Scheme
(15S)-15-methyl-PGF2α methyl ester 11-(trichloroethylcarbonate)
85720-17-8

(15S)-15-methyl-PGF2α methyl ester 11-(trichloroethylcarbonate)

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 60 percent / imidazole / dimethylformamide / 16 h / 80 °C
2: 89 percent / Zn, CH3OH / 1.25 h / Heating
3: 1.) 2 N aq. KOH, 2.) Ph3P / 1.) THF, CH3OH, 25 deg C, 4 h, 2.) xylene, 25 deg C, 90 min
4: xylene / 36 h / Heating
5: 42 percent / Bu4NF / 1,2-dimethoxy-ethane / 16 h / Heating
View Scheme
(15S)-15-methyl-PGF2α methyl ester 9,15bis(tert-butyldimethylsilyl ether)
85720-19-0

(15S)-15-methyl-PGF2α methyl ester 9,15bis(tert-butyldimethylsilyl ether)

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) 2 N aq. KOH, 2.) Ph3P / 1.) THF, CH3OH, 25 deg C, 4 h, 2.) xylene, 25 deg C, 90 min
2: xylene / 36 h / Heating
3: 42 percent / Bu4NF / 1,2-dimethoxy-ethane / 16 h / Heating
View Scheme
(Z)-7-{(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-oct-1-enyl]-3-hydroxy-cyclopentyl}-hept-5-enethioic acid S-pyridin-2-yl ester

(Z)-7-{(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-oct-1-enyl]-3-hydroxy-cyclopentyl}-hept-5-enethioic acid S-pyridin-2-yl ester

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: xylene / 36 h / Heating
2: 42 percent / Bu4NF / 1,2-dimethoxy-ethane / 16 h / Heating
View Scheme
(15S)-15-methyl-PGF2α methyl ester 9,15bis(tert-butyldimethylsilyl ether) 11-(trichloroethyl carbonate)
85720-18-9

(15S)-15-methyl-PGF2α methyl ester 9,15bis(tert-butyldimethylsilyl ether) 11-(trichloroethyl carbonate)

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 89 percent / Zn, CH3OH / 1.25 h / Heating
2: 1.) 2 N aq. KOH, 2.) Ph3P / 1.) THF, CH3OH, 25 deg C, 4 h, 2.) xylene, 25 deg C, 90 min
3: xylene / 36 h / Heating
4: 42 percent / Bu4NF / 1,2-dimethoxy-ethane / 16 h / Heating
View Scheme
(3aR,4R,5R,6aS)-5-triethylsilyloxy-4-[(1E,3S)-3-hydroxy-3-methyloct-1-en-1-yl]hexahydro-2H-cyclopenta[b]furan-2-ol
1036855-83-0

(3aR,4R,5R,6aS)-5-triethylsilyloxy-4-[(1E,3S)-3-hydroxy-3-methyloct-1-en-1-yl]hexahydro-2H-cyclopenta[b]furan-2-ol

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Wittig Reaction;
Multi-step reaction with 3 steps
1.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / -78 °C
1.2: 4 h / 20 °C
2.1: sodium carbonate / acetonitrile; water / 4 h / 20 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C
View Scheme
[1,1'-bisphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-hydroxy-4-[(1E)-3-hydroxy-3-methyl-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl ester

[1,1'-bisphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-hydroxy-4-[(1E)-3-hydroxy-3-methyl-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl ester

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium carbonate / methanol / 40 °C / Large scale
2: potassium tert-butylate / tetrahydrofuran / -10 - -5 °C / Inert atmosphere; Large scale
3: potassium carbonate / acetone / 50 °C / Large scale
4: sodium hydroxide; water / methanol
View Scheme
(3aR,4R,5R,6aS)-hexahydro-4-[(1E)-3-hydroxy-3-methyl-1-octen-1-yl]-2H-cyclopenta[b]furan-2,5-diol

(3aR,4R,5R,6aS)-hexahydro-4-[(1E)-3-hydroxy-3-methyl-1-octen-1-yl]-2H-cyclopenta[b]furan-2,5-diol

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium tert-butylate / tetrahydrofuran / -10 - -5 °C / Inert atmosphere; Large scale
2: potassium carbonate / acetone / 50 °C / Large scale
3: sodium hydroxide; water / methanol
View Scheme
(5Z,9α,11α,13E)-15-methyl-9,11,15-trihydroxy-prosta-5,13-diene-1-carboxylic acid
41691-84-3

(5Z,9α,11α,13E)-15-methyl-9,11,15-trihydroxy-prosta-5,13-diene-1-carboxylic acid

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / acetone / 50 °C / Large scale
2: sodium hydroxide; water / methanol
View Scheme
[1,1'-bisphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl ester
31753-00-1

[1,1'-bisphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl ester

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: (S,S)-taddol / toluene / -50 °C / Inert atmosphere; Large scale
2: diisobutylaluminium hydride / toluene; tetrahydrofuran / -75 °C / Inert atmosphere; Large scale
3: potassium carbonate / methanol / 40 °C / Large scale
4: potassium tert-butylate / tetrahydrofuran / -10 - -5 °C / Inert atmosphere; Large scale
5: potassium carbonate / acetone / 50 °C / Large scale
6: sodium hydroxide; water / methanol
View Scheme
[1,1'-bisphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-hydroxy-3-methyl-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl ester

[1,1'-bisphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-hydroxy-3-methyl-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl ester

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: diisobutylaluminium hydride / toluene; tetrahydrofuran / -75 °C / Inert atmosphere; Large scale
2: potassium carbonate / methanol / 40 °C / Large scale
3: potassium tert-butylate / tetrahydrofuran / -10 - -5 °C / Inert atmosphere; Large scale
4: potassium carbonate / acetone / 50 °C / Large scale
5: sodium hydroxide; water / methanol
View Scheme
(4-carboxybutyl)triphenylphosphonium bromide

(4-carboxybutyl)triphenylphosphonium bromide

C16H28O4

C16H28O4

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Stage #1: (4-carboxybutyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at -10 - -5℃; for 0.166667h; Wittig Olefination; Inert atmosphere;
Stage #2: C16H28O4 In tetrahydrofuran at -5℃; for 12h;
10.8 g
3α,5α-Dihydroxy-2β-(3'-oxo-trans-1'-octenyl)cyclopentane-1α-acetic acid γ-lactone 3-tert-butyldimethylsilyl ether
64072-25-9

3α,5α-Dihydroxy-2β-(3'-oxo-trans-1'-octenyl)cyclopentane-1α-acetic acid γ-lactone 3-tert-butyldimethylsilyl ether

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: tetrahydrofuran / 6 h / -50 °C / Inert atmosphere
2.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C
3.1: potassium tert-butylate / tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere
3.2: 4 h / 20 °C
4.1: lithium hydroxide; water / tetrahydrofuran / 2 h / 20 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C
View Scheme
C22H40O4Si

C22H40O4Si

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C
2.1: potassium tert-butylate / tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere
2.2: 4 h / 20 °C
3.1: lithium hydroxide; water / tetrahydrofuran / 2 h / 20 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C
View Scheme
C22H42O4Si

C22H42O4Si

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium tert-butylate / tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere
1.2: 4 h / 20 °C
2.1: lithium hydroxide; water / tetrahydrofuran / 2 h / 20 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C
View Scheme
C28H52O5Si

C28H52O5Si

Carboprost
35700-23-3

Carboprost

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium hydroxide; water / tetrahydrofuran / 2 h / 20 °C
2: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C
View Scheme
Carboprost
35700-23-3

Carboprost

2-amino-2-hydroxymethyl-1,3-propanediol
77-86-1

2-amino-2-hydroxymethyl-1,3-propanediol

carboprost tromethamine

carboprost tromethamine

Conditions
ConditionsYield
In methanol at 20℃; for 2h;100%
In isopropyl alcohol at 20℃; for 1h;
Carboprost
35700-23-3

Carboprost

(Z)-(1R,3aS,11aR)-1-((E)-(S)-3-Hydroxy-3-methyl-oct-1-enyl)-1,3,3a,6,7,8,11,11a-octahydro-4-oxa-cyclopentacyclodecene-2,5-dione
85235-19-4

(Z)-(1R,3aS,11aR)-1-((E)-(S)-3-Hydroxy-3-methyl-oct-1-enyl)-1,3,3a,6,7,8,11,11a-octahydro-4-oxa-cyclopentacyclodecene-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 79 percent / 2,2'-dipyridyl disulfide, PPh3 / xylene / a) 25 deg C, 18 h, b) reflux, 4 h
2: 440 mg / H2CrO4, H2SO4 / acetone / a) -40 deg C, 2 h, b) -30 deg C, 1.5 h
View Scheme
Carboprost
35700-23-3

Carboprost

(15S)-15-methyl-9-deoxy-Δ9-PGD2
85235-20-7

(15S)-15-methyl-9-deoxy-Δ9-PGD2

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 79 percent / 2,2'-dipyridyl disulfide, PPh3 / xylene / a) 25 deg C, 18 h, b) reflux, 4 h
2: 440 mg / H2CrO4, H2SO4 / acetone / a) -40 deg C, 2 h, b) -30 deg C, 1.5 h
3: 190 mg / silica gel / ethyl acetate; methanol
View Scheme
Carboprost
35700-23-3

Carboprost

U 36384
35700-21-1

U 36384

35700-23-3Relevant articles and documents

Concise, scalable and enantioselective total synthesis of prostaglandins

Zhang, Fuhao,Zeng, Jingwen,Gao, Mohan,Wang, Linzhou,Chen, Gen-Qiang,Lu, Yixin,Zhang, Xumu

, p. 692 - 697 (2021/06/01)

Prostaglandins are among the most important natural isolates owing to their broad range of bioactivities and unique structures. However, current methods for the synthesis of prostaglandins suffer from low yields and lengthy steps. Here, we report a practicability-oriented synthetic strategy for the enantioselective and divergent synthesis of prostaglandins. In this approach, the multiply substituted five-membered rings in prostaglandins were constructed via the key enyne cycloisomerization with excellent selectivity (>20:1 d.r., 98% e.e.). The crucial chiral centre on the scaffold of the prostaglandins was installed using the asymmetric hydrogenation method (up to 98% yield and 98% e.e.). From our versatile common intermediates, a series of prostaglandins and related drugs could be produced in two steps, and fluprostenol could be prepared on a 20-gram scale. [Figure not available: see fulltext.]

Preparation method of prostaglandin analogue

-

Paragraph 0258; 0280-0282, (2021/03/06)

The invention discloses a preparation method of a prostaglandin analogue, the prostaglandin analogue is a compound shown as a formula 9, the specific synthetic route is as follows: reagents and raw materials used in the invention are available on the market, and the preparation method has the advantages of mild reaction conditions, simple operation, low energy consumption and cost, and high yield,and is suitable for industrial production.

PROCESS FOR THE PREPARATION OF CARBOPROST AND ITS TROMETHAMINE SALT

-

, (2017/06/24)

The subject of the invention is a novel process for the preparation of Carboprost tromethamine salt where alkylation the enone of the general formula (II) is carried out in the presence of a chiral auxiliary in aprotic solvent with a Grignard reagent. The methyl ester epimers of formula (VII) are separated by gravity silicagel chromatography and the salt formation is carried out by using solid tromethamine base.

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