prop-2-en-1-yl (2S)-3-(benzyloxy)-2-{[(2S)-3-(benzyloxy)-2-{[(2S)-2-{[(2R,3R,4S,5R)-3,5-dihydroxy-2,4-dimethyloctadecanoyl]amino}-3-methylbutanoyl]amino}butanoyl]amino}propanoate

Base Information

• Chemical Name: prop-2-en-1-yl (2S)-3-(benzyloxy)-2-{[(2S)-3-(benzyloxy)-2-{[(2S)-2-{[(2R,3R,4S,5R)-3,5-dihydroxy-2,4-dimethyloctadecanoyl]amino}-3-methylbutanoyl]amino}butanoyl]amino}propanoate
• CAS No.: 452956-91-1
• Molecular Formula: C₄₉H₇₇N₃O₉
• Molecular Weight: 852.165

Synonyms:prop-2-en-1-yl (2S)-3-(benzyloxy)-2-{[(2S)-3-(benzyloxy)-2-{[(2S)-2-{[(2R,3R,4S,5R)-3,5-dihydroxy-2,4-dimethyloctadecanoyl]amino}-3-methylbutanoyl]amino}butanoyl]amino}propanoate

Chemical Property of prop-2-en-1-yl (2S)-3-(benzyloxy)-2-{[(2S)-3-(benzyloxy)-2-{[(2S)-2-{[(2R,3R,4S,5R)-3,5-dihydroxy-2,4-dimethyloctadecanoyl]amino}-3-methylbutanoyl]amino}butanoyl]amino}propanoate

Chemical Property:

Purity/Quality:

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Technology Process of prop-2-en-1-yl (2S)-3-(benzyloxy)-2-{[(2S)-3-(benzyloxy)-2-{[(2S)-2-{[(2R,3R,4S,5R)-3,5-dihydroxy-2,4-dimethyloctadecanoyl]amino}-3-methylbutanoyl]amino}butanoyl]amino}propanoate

There total 30 articles about prop-2-en-1-yl (2S)-3-(benzyloxy)-2-{[(2S)-3-(benzyloxy)-2-{[(2S)-2-{[(2R,3R,4S,5R)-3,5-dihydroxy-2,4-dimethyloctadecanoyl]amino}-3-methylbutanoyl]amino}butanoyl]amino}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:

(S)-3-Benzyloxy-2-((2S,3R)-3-benzyloxy-2-{(S)-3-methyl-2-[(R)-2-((4R,5S,6R)-2,2,5-trimethyl-6-tridecyl-[1,3]dioxan-4-yl)-propionylamino]-butyrylamino}-butyrylamino)-propionic acid allyl ester (864430-45-5) → prop-2-en-1-yl (2S)-3-(benzyloxy)-2-{[(2S)-3-(benzyloxy)-2-{[(2S)-2-{[(2R,3R,4S,5R)-3,5-dihydroxy-2,4-dimethyloctadecanoyl]amino}-3-methylbutanoyl]amino}butanoyl]amino}propanoate (452956-91-1)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2005.06.073

Reference yield:

[4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-2-oxo-butyl]-phosphonic acid diethyl ester (851121-38-5) → prop-2-en-1-yl (2S)-3-(benzyloxy)-2-{[(2S)-3-(benzyloxy)-2-{[(2S)-2-{[(2R,3R,4S,5R)-3,5-dihydroxy-2,4-dimethyloctadecanoyl]amino}-3-methylbutanoyl]amino}butanoyl]amino}propanoate (452956-91-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: n-BuLi / tetrahydrofuran / -78 - 20 °C

1.2: 75 percent / tetrahydrofuran / 3 h / -78 - 20 °C

2.1: 85 percent / DIBAL-H / toluene / 0.5 h / -78 °C

3.1: 90 percent / m-CPBA / 0.5 h / 0 - 20 °C

4.1: 75 percent / cyclohexa-1,4-diene; Zn; ZnCl₂ / Cp₂TiCl₂ / tetrahydrofuran / 8 h / -20 - 20 °C

5.1: CSA / 1 h / 0 - 20 °C

6.1: TBAF / tetrahydrofuran / 2 h / 0 - 20 °C

7.1: RuCl₃*3H₂O; NaIO₄ / acetonitrile; CCl₄; H₂O / 0.5 h / 0 °C

8.1: 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide*HCl; 1-hydroxybenzotriazole / CH₂Cl₂ / 0 °C

8.2: 65 percent / DIPEA / CH₂Cl₂ / 12 h / 0 - 20 °C

9.1: LiOH / tetrahydrofuran; methanol; H₂O / 1 h / 0 °C

10.1: DCC; DMAP / CH₂Cl₂ / 2 h / 0 °C

11.1: CSA / CH₂Cl₂ / 2 h / 0 - 20 °C

With dmap; ruthenium trichloride; lithium hydroxide; sodium periodate; n-butyllithium; cyclohexa-1,4-diene; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; zinc(II) chloride; zinc; bis(cyclopentadienyl)titanium dichloride; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; toluene; acetonitrile; 1.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1016/j.tetlet.2005.06.073

Reference yield:

(E)-(S)-1-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-octadec-4-en-3-one (864430-38-6) → prop-2-en-1-yl (2S)-3-(benzyloxy)-2-{[(2S)-3-(benzyloxy)-2-{[(2S)-2-{[(2R,3R,4S,5R)-3,5-dihydroxy-2,4-dimethyloctadecanoyl]amino}-3-methylbutanoyl]amino}butanoyl]amino}propanoate (452956-91-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 85 percent / DIBAL-H / toluene / 0.5 h / -78 °C

2.1: 90 percent / m-CPBA / 0.5 h / 0 - 20 °C

3.1: 75 percent / cyclohexa-1,4-diene; Zn; ZnCl₂ / Cp₂TiCl₂ / tetrahydrofuran / 8 h / -20 - 20 °C

4.1: CSA / 1 h / 0 - 20 °C

5.1: TBAF / tetrahydrofuran / 2 h / 0 - 20 °C

6.1: RuCl₃*3H₂O; NaIO₄ / acetonitrile; CCl₄; H₂O / 0.5 h / 0 °C

7.1: 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide*HCl; 1-hydroxybenzotriazole / CH₂Cl₂ / 0 °C

7.2: 65 percent / DIPEA / CH₂Cl₂ / 12 h / 0 - 20 °C

8.1: LiOH / tetrahydrofuran; methanol; H₂O / 1 h / 0 °C

9.1: DCC; DMAP / CH₂Cl₂ / 2 h / 0 °C

10.1: CSA / CH₂Cl₂ / 2 h / 0 - 20 °C

With dmap; ruthenium trichloride; lithium hydroxide; sodium periodate; cyclohexa-1,4-diene; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; zinc(II) chloride; zinc; bis(cyclopentadienyl)titanium dichloride; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; toluene; acetonitrile;

DOI:10.1016/j.tetlet.2005.06.073

upstream raw materials:

(S)-3-Benzyloxy-2-((2S,3R)-3-benzyloxy-2-{(S)-3-methyl-2-[(R)-2-((4R,5S,6R)-2,2,5-trimethyl-6-tridecyl-[1,3]dioxan-4-yl)-propionylamino]-butyrylamino}-butyrylamino)-propionic acid allyl ester

[4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-2-oxo-butyl]-phosphonic acid diethyl ester

(R)-2-((4R,5S,6R)-2,2,5-Trimethyl-6-tridecyl-[1,3]dioxan-4-yl)-propionic acid

(E)-(S)-1-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-octadec-4-en-3-one

Downstream raw materials:

(2S)-3-(benzyloxy)-2-{[(2S)-3-(benzyloxy)-2-{[(2S)-2-{[(2R,3R,4S,5R)-3,5-dihydroxy-2,4-dimethyloctadecanoyl]amino}-3-methylbutanoyl]amino}butanoyl]amino}propanoic acid

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