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

Base Information

Chemical Name:(1S,2S,4R,6S)-4-acetoxy-1-methyl-7-oxabicyclo[4.1.0]heptan-2-yl 4-nitrobenzoate
CAS No.:1259529-39-9
Molecular Formula:C₁₆H₁₇NO₇
Molecular Weight:335.313
Hs Code.:

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

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

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

There total 4 articles about (1S,2S,4R,6S)-4-acetoxy-1-methyl-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: 75.0%

: 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

: 108-24-7
acetic anhydride

: 1259529-39-9
(1S,2S,4R,6S)-4-acetoxy-1-methyl-7-oxabicyclo[4.1.0]heptan-2-yl 4-nitrobenzoate

Guidance literature:: (1S,2S,4R,6S)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-yl 4-nitrobenzoate; With sodium hydrogencarbonate; ozone; In methanol; dichloromethane; at -78 ℃; for 1.25h;

acetic anhydride; With dmap; triethylamine; In methanol; dichloromethane; at 0 ℃; for 12h; diastereoselective reaction; Reflux;
DOI:10.1021/ol102586w

Reference yield:

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

: 1259529-39-9
(1S,2S,4R,6S)-4-acetoxy-1-methyl-7-oxabicyclo[4.1.0]heptan-2-yl 4-nitrobenzoate

Guidance literature:: Multi-step reaction with 2 steps

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

2.1: sodium hydrogencarbonate; ozone / methanol; dichloromethane / 1.25 h / -78 °C

2.2: 12 h / 0 °C / Reflux

With di-isopropyl azodicarboxylate; sodium hydrogencarbonate; ozone; triphenylphosphine; In methanol; dichloromethane; toluene; 1.1: Mitsunobu reaction;
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

: 1259529-39-9
(1S,2S,4R,6S)-4-acetoxy-1-methyl-7-oxabicyclo[4.1.0]heptan-2-yl 4-nitrobenzoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / -40 - -30 °C

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

3.1: sodium hydrogencarbonate; ozone / methanol; dichloromethane / 1.25 h / -78 °C

3.2: 12 h / 0 °C / Reflux

With di-isopropyl azodicarboxylate; sodium hydrogencarbonate; ozone; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In methanol; dichloromethane; toluene; 2.1: Mitsunobu reaction;
DOI:10.1021/ol102586w