(S)-((3S,4R,5S,7S)-3,5,7-trimethyltridec-1-en-4-yl) 2-(benzyloxycarbonylamino)propanoate

Base Information

• Chemical Name: (S)-((3S,4R,5S,7S)-3,5,7-trimethyltridec-1-en-4-yl) 2-(benzyloxycarbonylamino)propanoate
• CAS No.: 1453811-68-1
• Molecular Formula: C₂₇H₄₃NO₄
• Molecular Weight: 445.643

Synonyms:(S)-((3S,4R,5S,7S)-3,5,7-trimethyltridec-1-en-4-yl) 2-(benzyloxycarbonylamino)propanoate

Chemical Property of (S)-((3S,4R,5S,7S)-3,5,7-trimethyltridec-1-en-4-yl) 2-(benzyloxycarbonylamino)propanoate

Chemical Property:

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Technology Process of (S)-((3S,4R,5S,7S)-3,5,7-trimethyltridec-1-en-4-yl) 2-(benzyloxycarbonylamino)propanoate

There total 11 articles about (S)-((3S,4R,5S,7S)-3,5,7-trimethyltridec-1-en-4-yl) 2-(benzyloxycarbonylamino)propanoate 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: 80.0%

(3S,4R,5S,7S)-3,5,7-trimethyl-tridec-1-en-4-ol (1147123-60-1) + N-Cbz-Ala (1142-20-7) → (S)-((3S,4R,5S,7S)-3,5,7-trimethyltridec-1-en-4-yl) 2-(benzyloxycarbonylamino)propanoate (1453811-68-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; for 5h;

DOI:10.1016/j.tetasy.2013.07.012

Reference yield:

(S)-α-methyloctanal (7786-29-0,49642-49-1,72598-55-1,55352-42-6) → (S)-((3S,4R,5S,7S)-3,5,7-trimethyltridec-1-en-4-yl) 2-(benzyloxycarbonylamino)propanoate (1453811-68-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: triethylamine; dicyclohexylboron chloride / diethyl ether / 2.5 h / -78 - 0 °C

1.2: -78 - 0 °C

2.1: tetramethylammonium triacetoxyborohydride / acetone; acetic acid / 30 h / -20 °C

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.5 h / 0 °C / Molecular sieve

4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C

4.2: 0.5 h / -78 °C

4.3: 0.08 h / -78 °C

5.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / 0.5 h / 120 °C

6.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 °C

7.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.17 h / 20 °C / Inert atmosphere; Molecular sieve

8.1: potassium tert-butylate / diethyl ether / 0.5 h / 0 - 20 °C

8.2: 0.5 h / 0 °C

9.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chloroform; water / 0.5 h / 0 °C

10.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 5 h / 0 - 20 °C

With dmap; tetrapropylammonium perruthennate; 2,2'-azobis(isobutyronitrile); dicyclohexylboron chloride; potassium tert-butylate; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; water; acetic acid; acetone; toluene; 7.1: |Ley Oxidation / 8.1: |Wittig Olefination / 8.2: |Wittig Olefination;

DOI:10.1016/j.tetasy.2013.07.012

Reference yield:

(2S,3S,4S,5S,6S)-1-(4-methoxybenzyloxy)-2,4,6-trimethyldodecane-3,5-diol (1453811-63-6) → (S)-((3S,4R,5S,7S)-3,5,7-trimethyltridec-1-en-4-yl) 2-(benzyloxycarbonylamino)propanoate (1453811-68-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.5 h / 0 °C / Molecular sieve

2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C

2.2: 0.5 h / -78 °C

2.3: 0.08 h / -78 °C

3.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / 0.5 h / 120 °C

4.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 °C

5.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.17 h / 20 °C / Inert atmosphere; Molecular sieve

6.1: potassium tert-butylate / diethyl ether / 0.5 h / 0 - 20 °C

6.2: 0.5 h / 0 °C

7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chloroform; water / 0.5 h / 0 °C

8.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 5 h / 0 - 20 °C

With dmap; tetrapropylammonium perruthennate; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; water; toluene; 5.1: |Ley Oxidation / 6.1: |Wittig Olefination / 6.2: |Wittig Olefination;

DOI:10.1016/j.tetasy.2013.07.012

upstream raw materials:

(S)-α-methyloctanal

(2S,4S,5S,6S)-5-hydroxy-1-(4-methoxybenzyloxy)-2,4,6-trimethyldodecan-3-one

(2S,3S,4S,5S,6S)-1-(4-methoxybenzyloxy)-2,4,6-trimethyldodecane-3,5-diol

(2S,3S,4S)-2-((4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-4-methyldecan-3-ol

Downstream raw materials:

((2R,3R,4S,6S)-1-(2-tert-butoxy-2-oxoethylamino)-2,4,6-trimethyl-1-oxododecan-3-yl) (S)-2-(benzyloxycarbonylamino)propanoate

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