(1S,2S,3S,4R)-3-{[(1S,2S,3S,4R)-3-(Allyl-tert-butoxycarbonyl-amino)-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-benzyl-amino}-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid allyl ester

Base Information

Chemical Name:(1S,2S,3S,4R)-3-{[(1S,2S,3S,4R)-3-(Allyl-tert-butoxycarbonyl-amino)-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-benzyl-amino}-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid allyl ester
CAS No.:792910-76-0
Molecular Formula:C₃₂H₃₈N₂O₇
Molecular Weight:562.663
Hs Code.:

(1S,2S,3S,4R)-3-{[(1S,2S,3S,4R)-3-(Allyl-tert-butoxycarbonyl-amino)-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-benzyl-amino}-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid allyl ester

Synonyms:(1S,2S,3S,4R)-3-{[(1S,2S,3S,4R)-3-(Allyl-tert-butoxycarbonyl-amino)-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-benzyl-amino}-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid allyl ester

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Chemical Property of (1S,2S,3S,4R)-3-{[(1S,2S,3S,4R)-3-(Allyl-tert-butoxycarbonyl-amino)-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-benzyl-amino}-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid allyl ester

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Technology Process of (1S,2S,3S,4R)-3-{[(1S,2S,3S,4R)-3-(Allyl-tert-butoxycarbonyl-amino)-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-benzyl-amino}-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid allyl ester

There total 8 articles about (1S,2S,3S,4R)-3-{[(1S,2S,3S,4R)-3-(Allyl-tert-butoxycarbonyl-amino)-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-benzyl-amino}-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid allyl ester 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: 39.0%

: Allyl-((1R,2S,3S,4S)-3-chlorocarbonyl-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl)-carbamic acid tert-butyl ester

: 792910-74-8
(1S,2S,3S,4R)-3-Benzylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid allyl ester

: 792910-76-0
(1S,2S,3S,4R)-3-{[(1S,2S,3S,4R)-3-(Allyl-tert-butoxycarbonyl-amino)-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-benzyl-amino}-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid allyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 1h;
DOI:10.1021/ol0484106

Reference yield:

: (1S,2S,3S,4R)-3-tert-Butoxycarbonylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

: 792910-76-0
(1S,2S,3S,4R)-3-{[(1S,2S,3S,4R)-3-(Allyl-tert-butoxycarbonyl-amino)-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-benzyl-amino}-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid allyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 88 percent / NaH / dimethylformamide / 1.5 h

2: LiOH*H₂O / methanol; H₂O / 2 h

3: (COCl)2; DMF / CH₂Cl₂ / 1 h / 0 - 20 °C

4: 39 percent / DIPEA / CH₂Cl₂ / 1 h / 0 - 20 °C

With lithium hydroxide; oxalyl dichloride; sodium hydride; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; In methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ol0484106

Reference yield:

: 100-39-0
benzyl bromide

: 792910-76-0
(1S,2S,3S,4R)-3-{[(1S,2S,3S,4R)-3-(Allyl-tert-butoxycarbonyl-amino)-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-benzyl-amino}-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid allyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 78 percent / NaH / dimethylformamide / 0.5 h / 20 °C

2.1: TFA / CH₂Cl₂ / 1 h / 0 - 20 °C

2.2: 56 percent / aq. KHCO₃ / CH₂Cl₂ / 0.75 h

3.1: 39 percent / DIPEA / CH₂Cl₂ / 1 h / 0 - 20 °C

With sodium hydride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol0484106