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

Base Information

Chemical Name:Allyl-[(1R,2S,3S,4S)-3-(allyl-benzyl-carbamoyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl]-carbamic acid tert-butyl ester
CAS No.:792910-70-4
Molecular Formula:C₂₅H₃₂N₂O₄
Molecular Weight:424.54
Hs Code.:

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

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Chemical Property of Allyl-[(1R,2S,3S,4S)-3-(allyl-benzyl-carbamoyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl]-carbamic acid tert-butyl ester

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Technology Process of Allyl-[(1R,2S,3S,4S)-3-(allyl-benzyl-carbamoyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl]-carbamic acid tert-butyl ester

There total 2 articles about Allyl-[(1R,2S,3S,4S)-3-(allyl-benzyl-carbamoyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl]-carbamic acid tert-butyl 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:

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

: 792910-70-4
Allyl-[(1R,2S,3S,4S)-3-(allyl-benzyl-carbamoyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 88 percent / NaH / dimethylformamide / 1.5 h

2: LiOH*H₂O / methanol; H₂O / 2 h

3: 55 percent / EDCI / CH₂Cl₂ / 14 h / 20 °C

With lithium hydroxide; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ol0484106

Reference yield:

: 792910-66-8
(1S,2S,3S,4R)-3-(Allyl-tert-butoxycarbonyl-amino)-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

: 792910-70-4
Allyl-[(1R,2S,3S,4S)-3-(allyl-benzyl-carbamoyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: LiOH*H₂O / methanol; H₂O / 2 h

2: 55 percent / EDCI / CH₂Cl₂ / 14 h / 20 °C

With lithium hydroxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In methanol; dichloromethane; water;
DOI:10.1021/ol0484106

Reference yield: 95.0%

: 74-85-1
ethene

: 792910-70-4
Allyl-[(1R,2S,3S,4S)-3-(allyl-benzyl-carbamoyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl]-carbamic acid tert-butyl ester

: (4aS,4bS,9aS,10aR)-6-Benzyl-5-oxo-3,4a,4b,5,6,7,9a,10a-octahydro-10-oxa-4,6-diaza-benzo[a]azulene-4-carboxylic acid tert-butyl ester

Guidance literature:: ethene; Allyl-[(1R,2S,3S,4S)-3-(allyl-benzyl-carbamoyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl]-carbamic acid tert-butyl ester; tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride; In dichloromethane; at 25 ℃; for 1h;

In dichloromethane; at 25 ℃; for 24h;
DOI:10.1021/ol0484106