N-<(R)-(E)-3-Hydroxy-5-(phenylthio)-4-pentenoyl>-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane

Base Information

• Chemical Name: N-<(R)-(E)-3-Hydroxy-5-(phenylthio)-4-pentenoyl>-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane
• CAS No.: 167260-00-6
• Molecular Formula: C₂₁H₂₅NO₃S₂
• Molecular Weight: 403.566

Synonyms:N-<(R)-(E)-3-Hydroxy-5-(phenylthio)-4-pentenoyl>-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane

Chemical Property of N-<(R)-(E)-3-Hydroxy-5-(phenylthio)-4-pentenoyl>-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane

Chemical Property:

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Technology Process of N-<(R)-(E)-3-Hydroxy-5-(phenylthio)-4-pentenoyl>-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane

There total 2 articles about N-<(R)-(E)-3-Hydroxy-5-(phenylthio)-4-pentenoyl>-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane 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:

(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.01,5>decane (147168-90-9) → N-<(R)-(E)-3-Hydroxy-5-(phenylthio)-4-pentenoyl>-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.01,5>decane (167260-00-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) sodium hydride / 1.) THF, 0 deg C, 25 min, 2.) THF, 0 deg C, 10 min

2: 1.) TiCl₄, diisopropylethylamine, 2.) TiCl₄ / 1.) CH₂Cl₂, -70 deg C, 20 min, 2.) CH₂Cl₂, -70 deg C, 0.5 h

With titanium tetrachloride; sodium hydride; N-ethyl-N,N-diisopropylamine;

Reference yield:

β-thiophenylacrolein (80227-71-0) + N-Acetyl-(1S,5R,7R)-10,10-Dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.01,5>decane (167259-92-9) → N-<(S)-(E)-3-Hydroxy-5-(phenylthio)-4-pentenoyl>-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.01,5>decane (167357-25-7) + N-<(R)-(E)-3-Hydroxy-5-(phenylthio)-4-pentenoyl>-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.01,5>decane (167260-00-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; 9-BBN triflate; Yield given. Multistep reaction. Yields of byproduct given; 1,) CH₂Cl₂, hexane, 0 deg C, 10 min; 0 deg C, 25 min, 2.) CH₂Cl₂, -78 deg C;

DOI:10.1021/jo00105a040

Reference yield: 65.0%

N-<(R)-(E)-3-Hydroxy-5-(phenylthio)-4-pentenoyl>-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.01,5>decane (167260-00-6) → (R)-(E)-3-Hydroxy-5-(phenylthio)-4-pentenoic acid

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; at -70 ℃; for 0.5h;

upstream raw materials:

β-thiophenylacrolein

N-Acetyl-(1S,5R,7R)-10,10-Dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane

(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane

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