(1R,2R,3S,4S)-<3--2-bornyl>-(6S)-2-hydroxy-6-isopropenyl-cyclohexenecarboxylate

Base Information

• Chemical Name: (1R,2R,3S,4S)-<3--2-bornyl>-(6S)-2-hydroxy-6-isopropenyl-cyclohexenecarboxylate
• CAS No.: 170117-07-4
• Molecular Formula: C₃₄H₄₃NO₅S
• Molecular Weight: 577.785

Synonyms:(1R,2R,3S,4S)-<3--2-bornyl>-(6S)-2-hydroxy-6-isopropenyl-cyclohexenecarboxylate

Chemical Property of (1R,2R,3S,4S)-<3--2-bornyl>-(6S)-2-hydroxy-6-isopropenyl-cyclohexenecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (1R,2R,3S,4S)-<3--2-bornyl>-(6S)-2-hydroxy-6-isopropenyl-cyclohexenecarboxylate

There total 6 articles about (1R,2R,3S,4S)-<3--2-bornyl>-(6S)-2-hydroxy-6-isopropenyl-cyclohexenecarboxylate 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: 62.0%

2-bromoprop-1-ene (557-93-7) + (1R,2R,3S,4S)-<3--2-bornyl>-2-oxo-cyclohexenecarboxylate (170117-11-0) → (1R,2R,3S,4S)-<3--2-bornyl>-(6S)-2-hydroxy-6-isopropenyl-cyclohexenecarboxylate (170117-07-4)

Guidance literature:

With tert.-butyl lithium; thien-2-yl(cyano)copper lithium; In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1016/0040-4020(95)00676-Y

Reference yield:

N-(3,5-Dimethyl-phenyl)-N-((1S,2S,3R,4R)-3-hydroxy-4,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl)-benzenesulfonamide (87360-02-9) → (1R,2R,3S,4S)-<3--2-bornyl>-(6S)-2-hydroxy-6-isopropenyl-cyclohexenecarboxylate (170117-07-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / DMAP / toluene / 48 h / Heating

2: pyridine / CH₂Cl₂ / 2 h / 20 °C

3: 91 percent / mCPBA / CH₂Cl₂ / 2 h / 20 °C

4: 62 percent / lithium 2-thienyl-cyanocuprate, t-BuLi / tetrahydrofuran / 2 h / -78 °C

With pyridine; dmap; tert.-butyl lithium; thien-2-yl(cyano)copper lithium; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/0040-4020(95)00676-Y

Reference yield:

(1R,2R,3S,4S)-<3--2-bornyl>-2-hydroxy-cyclohexenecarboxylate (170116-93-5) → (1R,2R,3S,4S)-<3--2-bornyl>-(6S)-2-hydroxy-6-isopropenyl-cyclohexenecarboxylate (170117-07-4)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / CH₂Cl₂ / 2 h / 20 °C

2: 91 percent / mCPBA / CH₂Cl₂ / 2 h / 20 °C

3: 62 percent / lithium 2-thienyl-cyanocuprate, t-BuLi / tetrahydrofuran / 2 h / -78 °C

With pyridine; tert.-butyl lithium; thien-2-yl(cyano)copper lithium; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0040-4020(95)00676-Y

upstream raw materials:

isopropenyllithium

(1R,2R,3S,4S)-<3--2-bornyl>-2-oxo-cyclohexenecarboxylate

2-bromoprop-1-ene

N-(3,5-Dimethyl-phenyl)-N-((1S,2S,3R,4R)-3-hydroxy-4,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl)-benzenesulfonamide

Downstream raw materials:

N-(3,5-Dimethyl-phenyl)-N-((1S,2S,3R,4R)-3-hydroxy-4,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl)-benzenesulfonamide

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