2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid ethyl ester

Base Information

• Chemical Name: 2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid ethyl ester
• CAS No.: 1355990-07-6
• Molecular Formula: C₂₅H₃₈O₅
• Molecular Weight: 418.574
• Mol file: 1355990-07-6.mol

Synonyms:2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid ethyl ester

Chemical Property of 2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid ethyl ester

Chemical Property:

Purity/Quality:

>95% ^*data from raw suppliers

TreprostinilEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Treprostinil Ethyl Ester is a derivative of Treprostinil (T719500), Synthetic analog of Prostacyclin (P839060). Antihypertensive. Treprostinil, marketed under the trade name Remodulin is a medication used to treat pulmonary arterial hypertension (PAH).

Technology Process of 2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid ethyl ester

There total 53 articles about 2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid ethyl 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: 96.0%

ethyl bromoacetate (105-36-2) + (1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-1-((S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalene-2,5-diol (101692-02-8) → 2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid ethyl ester (1355990-07-6)

Guidance literature:

With potassium carbonate; potassium iodide; In acetone; for 16h; Inert atmosphere; Reflux;

Reference yield: 88.0%

ethanol (64-17-5) + treprostinil (81846-19-7) → 2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid ethyl ester (1355990-07-6)

Guidance literature:

With sulfuric acid; at 0 - 86 ℃; for 16h; Inert atmosphere;

DOI:10.1016/j.tetlet.2019.151428

Reference yield: 68.0%

tetra-(n-butyl)ammonium iodide (311-28-4) + ethyl bromoacetate (105-36-2) + (1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-1-((S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalene-2,5-diol (101692-02-8) → 2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid ethyl ester (1355990-07-6)

Guidance literature:

ethyl bromoacetate; (1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-1-((S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalene-2,5-diol; With potassium carbonate; In ethanol; at 20 ℃;

tetra-(n-butyl)ammonium iodide; In ethanol; Reflux;

upstream raw materials:

3-allyloxy-benzaldehyde

ethyl bromoacetate

(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-1-((S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalene-2,5-diol

meta-hydroxybenzaldehyde

Downstream raw materials:

treprostinil

Refernces

• 1、 Brocchini, Steve,Clapp, Lucie H.,Laing, Peter,Picken, Christina,Shen, Lei. "Synthetic routes to treprostinil N-acyl methylsulfonamide". . . Retrieved 2019.
• 2、 -. "PROSTACYCLIN COMPOUNDS, COMPOSITIONS AND METHODS OF USE THEREOF". Paragraph 00274; 00275; 00276. . Retrieved 2016/11/17.