(S)-[(3R,5S)-5-(benzyloxy)oct-1-en-3-yl] 3-[4-(2-(benzyloxy)ethoxy)phenyl]-2-[(R)-N,6-dimethyloct-7-enamido]propanoate

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Chemical Name:(S)-[(3R,5S)-5-(benzyloxy)oct-1-en-3-yl] 3-[4-(2-(benzyloxy)ethoxy)phenyl]-2-[(R)-N,6-dimethyloct-7-enamido]propanoate
CAS No.:1388220-68-5
Molecular Formula:C₄₃H₅₇NO₆
Molecular Weight:683.929
Hs Code.:

Synonyms:(S)-[(3R,5S)-5-(benzyloxy)oct-1-en-3-yl] 3-[4-(2-(benzyloxy)ethoxy)phenyl]-2-[(R)-N,6-dimethyloct-7-enamido]propanoate

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Chemical Property of (S)-[(3R,5S)-5-(benzyloxy)oct-1-en-3-yl] 3-[4-(2-(benzyloxy)ethoxy)phenyl]-2-[(R)-N,6-dimethyloct-7-enamido]propanoate

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Technology Process of (S)-[(3R,5S)-5-(benzyloxy)oct-1-en-3-yl] 3-[4-(2-(benzyloxy)ethoxy)phenyl]-2-[(R)-N,6-dimethyloct-7-enamido]propanoate

There total 14 articles about (S)-[(3R,5S)-5-(benzyloxy)oct-1-en-3-yl] 3-[4-(2-(benzyloxy)ethoxy)phenyl]-2-[(R)-N,6-dimethyloct-7-enamido]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: 78.0%

: (R)-6-methyloct-7-enoic acid

: 1388220-69-6
(S)-[(3R,5S)-5-(benzyloxy)oct-1-en-3-yl] 3-[4-(2-(benzyloxy)ethoxy)phenyl]-2-[tert-butoxycarbonyl(methyl)amino]propanoate

: 1388220-68-5
(S)-[(3R,5S)-5-(benzyloxy)oct-1-en-3-yl] 3-[4-(2-(benzyloxy)ethoxy)phenyl]-2-[(R)-N,6-dimethyloct-7-enamido]propanoate

Guidance literature:: (S)-[(3R,5S)-5-(benzyloxy)oct-1-en-3-yl] 3-[4-(2-(benzyloxy)ethoxy)phenyl]-2-[tert-butoxycarbonyl(methyl)amino]propanoate; With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere;

(R)-6-methyloct-7-enoic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 12h; Inert atmosphere;
DOI:10.1016/j.tetasy.2012.05.013

Reference yield:

: C₁₈H₂₅NO₆

: 1388220-68-5
(S)-[(3R,5S)-5-(benzyloxy)oct-1-en-3-yl] 3-[4-(2-(benzyloxy)ethoxy)phenyl]-2-[(R)-N,6-dimethyloct-7-enamido]propanoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C / Inert atmosphere

2.1: silver(l) oxide / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere

3.1: lithium hydroxide / tetrahydrofuran; methanol; water / 6 h / 0 - 20 °C / Inert atmosphere

4.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

5.1: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

5.2: 12 h / 0 - 20 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; dicyclohexyl-carbodiimide; trifluoroacetic acid; silver(l) oxide; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.tetasy.2012.05.013

Reference yield:

: 1035455-07-2
C₁₃H₁₈O₂

: 1388220-68-5
(S)-[(3R,5S)-5-(benzyloxy)oct-1-en-3-yl] 3-[4-(2-(benzyloxy)ethoxy)phenyl]-2-[(R)-N,6-dimethyloct-7-enamido]propanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: tetrahydrofuran / 1 h / -20 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate; Cumene hydroperoxide / dichloromethane / 12 h / -20 - 0 °C / Inert atmosphere; Molecular sieve

3.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

4.1: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

4.2: 12 h / 0 - 20 °C / Inert atmosphere

With titanium(IV) isopropylate; dmap; L-(+)-diisopropyl tartrate; Cumene hydroperoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; 2.1: Sharpless kinetic resolution;
DOI:10.1016/j.tetasy.2012.05.013