(1S,2S,3S,4R)-3-[[(1S,2S,3S,4R)-3-(Allyl-tert-butoxycarbonyl-amino)-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethyl]-(toluene-4-sulfonyl)-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-en-2-ylmethyl]-(toluene-4-sulfonyl)-amino]-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid allyl ester
CAS No.:792911-04-7
Molecular Formula:C₃₂H₄₀N₂O₈S
Molecular Weight:612.744
Hs Code.:

(1S,2S,3S,4R)-3-[[(1S,2S,3S,4R)-3-(Allyl-tert-butoxycarbonyl-amino)-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethyl]-(toluene-4-sulfonyl)-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-en-2-ylmethyl]-(toluene-4-sulfonyl)-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-en-2-ylmethyl]-(toluene-4-sulfonyl)-amino]-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid allyl ester

There total 6 articles about (1S,2S,3S,4R)-3-[[(1S,2S,3S,4R)-3-(Allyl-tert-butoxycarbonyl-amino)-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethyl]-(toluene-4-sulfonyl)-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:

: 98-59-9
p-toluenesulfonyl chloride

: 792910-98-6
(1S,2S,3S,4R)-3-Amino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid allyl ester

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

: (1S,2S,3S,4R)-3-[[(E)-3-(Allyl-tert-butoxycarbonyl-amino)-allyl]-(toluene-4-sulfonyl)-amino]-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid allyl ester

: 792911-04-7
(1S,2S,3S,4R)-3-[[(1S,2S,3S,4R)-3-(Allyl-tert-butoxycarbonyl-amino)-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethyl]-(toluene-4-sulfonyl)-amino]-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid allyl ester

Guidance literature:: (1S,2S,3S,4R)-3-Amino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid allyl ester; Allyl-((1R,2S,3S,4S)-3-formyl-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl)-carbamic acid tert-butyl ester; With sodium tris(acetoxy)borohydride; In dichloromethane; for 24h;

p-toluenesulfonyl chloride; With dmap; triethylamine; In dichloromethane; at 20 ℃; for 24h;
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

: 792911-04-7
(1S,2S,3S,4R)-3-[[(1S,2S,3S,4R)-3-(Allyl-tert-butoxycarbonyl-amino)-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethyl]-(toluene-4-sulfonyl)-amino]-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid allyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 88 percent / NaH / dimethylformamide / 1.5 h

2.1: 83 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

3.1: NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 2 h

4.1: NaBH(OAc)3 / CH₂Cl₂ / 24 h

4.2: 23.7 mg / DMAP; Et₃N / CH₂Cl₂ / 24 h / 20 °C

With lithium aluminium tetrahydride; sodium tris(acetoxy)borohydride; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; 3.1: Dess-Martin oxidation;
DOI:10.1021/ol0484106

Reference yield:

: 792910-58-8,148257-14-1
(1S,2S,3S,4R)-3-tert-Butoxycarbonylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

: 792911-04-7
(1S,2S,3S,4R)-3-[[(1S,2S,3S,4R)-3-(Allyl-tert-butoxycarbonyl-amino)-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethyl]-(toluene-4-sulfonyl)-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: Cs₂CO₃ / methanol; H₂O / pH 7

1.2: 66 percent / dimethylformamide / 20 °C

2.1: TFA / CH₂Cl₂ / 0.5 h

2.2: 100 percent / aq. KHCO₃

3.1: NaBH(OAc)3 / CH₂Cl₂ / 24 h

3.2: 23.7 mg / DMAP; Et₃N / CH₂Cl₂ / 24 h / 20 °C

With sodium tris(acetoxy)borohydride; caesium carbonate; trifluoroacetic acid; In methanol; dichloromethane; water;
DOI:10.1021/ol0484106