(1R,2S,6R,7S)-5-Methoxy-4-(4-phenylsulfanyl-but-3-ynyl)-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-3-one

Base Information

• Chemical Name: (1R,2S,6R,7S)-5-Methoxy-4-(4-phenylsulfanyl-but-3-ynyl)-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-3-one
• CAS No.: 139751-00-1
• Molecular Formula: C₂₀H₂₁NO₂S
• Molecular Weight: 339.458

Synonyms:(1R,2S,6R,7S)-5-Methoxy-4-(4-phenylsulfanyl-but-3-ynyl)-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-3-one

Chemical Property of (1R,2S,6R,7S)-5-Methoxy-4-(4-phenylsulfanyl-but-3-ynyl)-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-3-one

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (1R,2S,6R,7S)-5-Methoxy-4-(4-phenylsulfanyl-but-3-ynyl)-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-3-one

There total 2 articles about (1R,2S,6R,7S)-5-Methoxy-4-(4-phenylsulfanyl-but-3-ynyl)-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-3-one 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: 96.0%

(1R,2S,6R,7S)-4-But-3-ynyl-5-methoxy-4-aza-tricyclo[5.2.1.02,6]dec-8-en-3-one (139750-99-5) + diphenyldisulfane (882-33-7) → (1R,2S,6R,7S)-5-Methoxy-4-(4-phenylsulfanyl-but-3-ynyl)-4-aza-tricyclo[5.2.1.02,6]dec-8-en-3-one (139751-00-1)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; for 1h; -70 deg C - r. t.;

DOI:10.1246/cl.1991.2135

Reference yield:

(1R,2S,5R/S,6R,7S)-(+)-4-(but-3'-ynyl)-5-hydroxy-4-azatricyclo<5.2.1.02,6>dec-8-en-3-one (139750-90-6,139894-06-7) → (1R,2S,6R,7S)-5-Methoxy-4-(4-phenylsulfanyl-but-3-ynyl)-4-aza-tricyclo[5.2.1.02,6]dec-8-en-3-one (139751-00-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / pyridinium p-toluenesulfonate / 15 h / Ambient temperature

2: 96 percent / lithium hexamethyldisilazide / tetrahydrofuran / 1 h / -70 deg C - r. t.

With pyridinium p-toluenesulfonate; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1246/cl.1991.2135

Reference yield: 80.0%

formic acid (64-18-6) + (1R,2S,6R,7S)-5-Methoxy-4-(4-phenylsulfanyl-but-3-ynyl)-4-aza-tricyclo[5.2.1.02,6]dec-8-en-3-one (139751-00-1) → S-phenyl (1S,2R,3R,4S,9S,10R)-(+)-8-oxo-7-azatetracyclo<8.2.1.02,9.03,7>tridec-11-ene-4-carbothioate (139751-01-2)

Guidance literature:

for 15h; Ambient temperature;

DOI:10.1246/cl.1991.2135

upstream raw materials:

(1R,2S,6R,7S)-4-But-3-ynyl-5-methoxy-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-3-one

diphenyldisulfane

(1R,2S,5R/S,6R,7S)-(+)-4-(but-3'-ynyl)-5-hydroxy-4-azatricyclo<5.2.1.0^2,6>dec-8-en-3-one

Downstream raw materials:

S-phenyl (1S,2R,3R,4S,9S,10R)-(+)-8-oxo-7-azatetracyclo<8.2.1.0^2,9.0^3,7>tridec-11-ene-4-carbothioate

(+)-laburnine

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