(3R,5R)-9-(benzyloxy)-3-methylnon-1-en-7-yn-5-yl N-[(2S,4R)-2,4-dimethylhex-5-enoyl]-N-methyl-D-phenylalaninate

Base Information

• Chemical Name: (3R,5R)-9-(benzyloxy)-3-methylnon-1-en-7-yn-5-yl N-[(2S,4R)-2,4-dimethylhex-5-enoyl]-N-methyl-D-phenylalaninate
• CAS No.: 1472660-31-3
• Molecular Formula: C₃₅H₄₅NO₄
• Molecular Weight: 543.747

Synonyms:(3R,5R)-9-(benzyloxy)-3-methylnon-1-en-7-yn-5-yl N-[(2S,4R)-2,4-dimethylhex-5-enoyl]-N-methyl-D-phenylalaninate

Chemical Property of (3R,5R)-9-(benzyloxy)-3-methylnon-1-en-7-yn-5-yl N-[(2S,4R)-2,4-dimethylhex-5-enoyl]-N-methyl-D-phenylalaninate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5R)-9-(benzyloxy)-3-methylnon-1-en-7-yn-5-yl N-[(2S,4R)-2,4-dimethylhex-5-enoyl]-N-methyl-D-phenylalaninate

There total 22 articles about (3R,5R)-9-(benzyloxy)-3-methylnon-1-en-7-yn-5-yl N-[(2S,4R)-2,4-dimethylhex-5-enoyl]-N-methyl-D-phenylalaninate 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: 70.0%

(3R,5R)-9-(benzyloxy)-3-methylnon-1-en-7-yn-5-yl N-methyl-D-phenylalaninate (1472660-29-9) + (2S,4R)-2,4-dimethyl-5-hexenoic acid (116179-65-8) → (3R,5R)-9-(benzyloxy)-3-methylnon-1-en-7-yn-5-yl N-[(2S,4R)-2,4-dimethylhex-5-enoyl]-N-methyl-D-phenylalaninate (1472660-31-3)

Guidance literature:

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1002/hlca.201200519

Reference yield:

(E)-(S)-3-(1,4-Dioxa-spiro[4.5]dec-2-yl)-acrylic acid ethyl ester → (3R,5R)-9-(benzyloxy)-3-methylnon-1-en-7-yn-5-yl N-[(2S,4R)-2,4-dimethylhex-5-enoyl]-N-methyl-D-phenylalaninate (1472660-31-3)

Guidance literature:

Multi-step reaction with 17 steps

1.1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / 1 h / 0 °C / Inert atmosphere

2.1: water; lithium hydroxide / methanol; tetrahydrofuran / 10 h

3.1: triethylamine / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere

4.1: lithium chloride / tetrahydrofuran / 5 h / -20 - 0 °C / Inert atmosphere

5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

5.2: 3 h / -78 °C / Inert atmosphere

6.1: lithium borohydride / methanol; tetrahydrofuran; diethyl ether / 1 h / -10 °C / Inert atmosphere

7.1: pyridine; dmap / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

8.1: Dowex 50WX₈ / methanol / 48 h / 20 °C / Inert atmosphere

9.1: sodium hydride / tetrahydrofuran; mineral oil / 0.67 h / 0 - 20 °C / Inert atmosphere

9.2: 0.5 h / 0 - 20 °C / Inert atmosphere

10.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C / Inert atmosphere

10.2: 0.67 h / -78 °C / Inert atmosphere

11.1: diisobutylaluminium hydride / dichloromethane; hexane / 0.67 h / -78 °C / Inert atmosphere

12.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 3 h / 20 °C

13.1: diisobutylaluminium hydride / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

14.1: sodium hexamethyldisilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere

14.2: 5 h / -78 - 0 °C / Inert atmosphere

15.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 10 h / 0 - 20 °C / Inert atmosphere

16.1: trifluoroacetic acid / dichloromethane / 3 h / 0 - 23 °C / Inert atmosphere

17.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / dichloromethane / 0 - 20 °C / Inert atmosphere

With pyridine; dmap; sodium tetrahydroborate; lithium borohydride; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; nickel(II) chloride hexahydrate; [bis(acetoxy)iodo]benzene; di-isopropyl azodicarboxylate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; water; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; lithium chloride; lithium hydroxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; toluene; mineral oil; 14.1: |Wittig Olefination / 14.2: |Wittig Olefination;

DOI:10.1002/hlca.201200519

Reference yield:

(2R,4S)-8-(benzyloxy)-2-methyloct-6-yne-1,4-diol (1472660-18-6) → (3R,5R)-9-(benzyloxy)-3-methylnon-1-en-7-yn-5-yl N-[(2S,4R)-2,4-dimethylhex-5-enoyl]-N-methyl-D-phenylalaninate (1472660-31-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 3 h / 20 °C

2.1: diisobutylaluminium hydride / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

3.1: sodium hexamethyldisilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere

3.2: 5 h / -78 - 0 °C / Inert atmosphere

4.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 10 h / 0 - 20 °C / Inert atmosphere

5.1: trifluoroacetic acid / dichloromethane / 3 h / 0 - 23 °C / Inert atmosphere

6.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / dichloromethane / 0 - 20 °C / Inert atmosphere

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; di-isopropyl azodicarboxylate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; sodium hexamethyldisilazane; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; toluene; 3.1: |Wittig Olefination / 3.2: |Wittig Olefination;

DOI:10.1002/hlca.201200519

upstream raw materials:

(2R,4S)-8-(benzyloxy)-2-methyloct-6-yne-1,4-diol

(3R,5S)-5-[4-(benzyloxy)but-2-yn-1-yl]-3-methyldihydrofuran-2(3H)-one

(3R,5S)-9-(benzyloxy)-3-methylnon-1-en-7-yn-5-ol

C₁₇H₃₀O₄

Downstream raw materials:

(3R,6S,8R,11R,13R)-3-benzyl-13-[4-(benzyloxy)but-2-yn-1-yl]-4,6,8,11-tetramethyl-1-oxa-4-azacyclotridec-9-ene-2,5-dione

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