(R)-2-amino-3-(((2E,6E,10E)-3,7,11-trimethyl-12-(2,3,4,5,6-d₅-phenylamino)dodeca-2,6,10-trien-1-yl)thio)propanoic acid

Base Information

• Chemical Name: (R)-2-amino-3-(((2E,6E,10E)-3,7,11-trimethyl-12-(2,3,4,5,6-d₅-phenylamino)dodeca-2,6,10-trien-1-yl)thio)propanoic acid
• CAS No.: 1448620-62-9
• Molecular Formula: C₂₄H₃₆N₂O₂S
• Molecular Weight: 421.588

Synonyms:

Chemical Property of (R)-2-amino-3-(((2E,6E,10E)-3,7,11-trimethyl-12-(2,3,4,5,6-d₅-phenylamino)dodeca-2,6,10-trien-1-yl)thio)propanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (R)-2-amino-3-(((2E,6E,10E)-3,7,11-trimethyl-12-(2,3,4,5,6-d₅-phenylamino)dodeca-2,6,10-trien-1-yl)thio)propanoic acid

There total 6 articles about (R)-2-amino-3-(((2E,6E,10E)-3,7,11-trimethyl-12-(2,3,4,5,6-d₅-phenylamino)dodeca-2,6,10-trien-1-yl)thio)propanoic acid 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: 52.0%

(R)-methyl 2-amino-3-(((2E,6E,10E)-3,7,11-trimethyl-12-(2,3,4,5,6-d5-phenylamino)dodeca-2,6,10-trien-1-yl)thio)propanoate (1448620-60-7) → (R)-2-amino-3-(((2E,6E,10E)-3,7,11-trimethyl-12-(2,3,4,5,6-d5-phenylamino)dodeca-2,6,10-trien-1-yl)thio)propanoic acid (1448620-62-9)

Guidance literature:

With lithium hydroxide; In water; isopropyl alcohol;

DOI:10.1002/jlcr.3049

Reference yield:

(2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate (37905-02-5) → (R)-2-amino-3-(((2E,6E,10E)-3,7,11-trimethyl-12-(2,3,4,5,6-d5-phenylamino)dodeca-2,6,10-trien-1-yl)thio)propanoic acid (1448620-62-9)

Guidance literature:

Multi-step reaction with 6 steps

1: acetic acid / 1,2-dichloro-ethane / 0.33 h / 20 °C

2: sodium tris(acetoxy)borohydride / tetrahydrofuran

3: potassium carbonate / water; methanol / 20 °C

4: dibromotriphenylphosphorane; N-ethyl-N,N-diisopropylamine / acetonitrile / 0.78 h / 0 °C

5: methanol / 5 h / -20 °C

6: lithium hydroxide / water; isopropyl alcohol

With sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; lithium hydroxide; dibromotriphenylphosphorane; In tetrahydrofuran; methanol; water; 1,2-dichloro-ethane; isopropyl alcohol; acetonitrile; 1: |Wittig Olefination;

DOI:10.1002/jlcr.3049

Reference yield:

(2E,6E)-farnesyl acetate (4128-17-0) → (R)-2-amino-3-(((2E,6E,10E)-3,7,11-trimethyl-12-(2,3,4,5,6-d5-phenylamino)dodeca-2,6,10-trien-1-yl)thio)propanoic acid (1448620-62-9)

Guidance literature:

Multi-step reaction with 7 steps

1: selenium(IV) oxide

2: acetic acid / 1,2-dichloro-ethane / 0.33 h / 20 °C

3: sodium tris(acetoxy)borohydride / tetrahydrofuran

4: potassium carbonate / water; methanol / 20 °C

5: dibromotriphenylphosphorane; N-ethyl-N,N-diisopropylamine / acetonitrile / 0.78 h / 0 °C

6: methanol / 5 h / -20 °C

7: lithium hydroxide / water; isopropyl alcohol

With selenium(IV) oxide; sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; lithium hydroxide; dibromotriphenylphosphorane; In tetrahydrofuran; methanol; water; 1,2-dichloro-ethane; isopropyl alcohol; acetonitrile; 2: |Wittig Olefination;

DOI:10.1002/jlcr.3049

upstream raw materials:

(2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate

(2E,6E,10E)-3,7,11-trimethyl-12-(d₅-phenylamino)dodeca-2,6,10-trien-1-yl acetate

(R)-methyl 2-amino-3-(((2E,6E,10E)-3,7,11-trimethyl-12-(2,3,4,5,6-d₅-phenylamino)dodeca-2,6,10-trien-1-yl)thio)propanoate

(2E,6E)-farnesyl acetate

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