(1S,2S,4R,6S)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-yl 4-nitrobenzoate

Base Information

Chemical Name:(1S,2S,4R,6S)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-yl 4-nitrobenzoate
CAS No.:1259529-38-8
Molecular Formula:C₁₇H₁₉NO₅
Molecular Weight:317.342
Hs Code.:

Synonyms:(1S,2S,4R,6S)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-yl 4-nitrobenzoate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1S,2S,4R,6S)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-yl 4-nitrobenzoate

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Technology Process of (1S,2S,4R,6S)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-yl 4-nitrobenzoate

There total 3 articles about (1S,2S,4R,6S)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-yl 4-nitrobenzoate 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: 80.0%

: 24120-79-4
(1R,2R,4S,6S)-(-)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-ol

: 62-23-7
4-nitro-benzoic acid

: 1259529-38-8
(1S,2S,4R,6S)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-yl 4-nitrobenzoate

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; at -10 - 20 ℃; Inert atmosphere;
DOI:10.1021/ol102586w

Reference yield:

: 99-48-9,1197-06-4,1197-07-5,2102-58-1,2102-59-2,5157-78-8,5503-11-7,7632-16-8,18383-51-2,22567-18-6,20307-86-2
(4R,6R)-carveol

: 1259529-38-8
(1S,2S,4R,6S)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-yl 4-nitrobenzoate

Guidance literature:: Multi-step reaction with 2 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / -40 - -30 °C

2: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / -10 - 20 °C / Inert atmosphere

With di-isopropyl azodicarboxylate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In dichloromethane; toluene; 2: Mitsunobu reaction;
DOI:10.1021/ol102586w

Reference yield:

: 6485-40-1,2244-16-8
(R)-Carvone

: 1259529-38-8
(1S,2S,4R,6S)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-yl 4-nitrobenzoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium aluminium tetrahydride / dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere

1.2: 1 h / 20 °C

2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / -40 - -30 °C

3.1: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / -10 - 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In dichloromethane; toluene; 3.1: Mitsunobu reaction;
DOI:10.1021/ol102586w