(2S,3S,3aS,7aR)-3-{[((2R,3S,3aS,8aS)-4-Oxo-2-vinyl-2,3,3a,4,6,8a-hexahydro-furo[3,2-c]oxepin-3-yl)-(toluene-4-sulfonyl)-amino]-methyl}-2-vinyl-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyridine-4-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2S,3S,3aS,7aR)-3-{[((2R,3S,3aS,8aS)-4-Oxo-2-vinyl-2,3,3a,4,6,8a-hexahydro-furo[3,2-c]oxepin-3-yl)-(toluene-4-sulfonyl)-amino]-methyl}-2-vinyl-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyridine-4-carboxylic acid tert-butyl ester
CAS No.:792910-93-1
Molecular Formula:C₃₂H₄₀N₂O₈S
Molecular Weight:612.744
Hs Code.:

(2S,3S,3aS,7aR)-3-{[((2R,3S,3aS,8aS)-4-Oxo-2-vinyl-2,3,3a,4,6,8a-hexahydro-furo[3,2-c]oxepin-3-yl)-(toluene-4-sulfonyl)-amino]-methyl}-2-vinyl-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyridine-4-carboxylic acid tert-butyl ester

Synonyms:(2S,3S,3aS,7aR)-3-{[((2R,3S,3aS,8aS)-4-Oxo-2-vinyl-2,3,3a,4,6,8a-hexahydro-furo[3,2-c]oxepin-3-yl)-(toluene-4-sulfonyl)-amino]-methyl}-2-vinyl-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyridine-4-carboxylic acid tert-butyl ester

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Chemical Property of (2S,3S,3aS,7aR)-3-{[((2R,3S,3aS,8aS)-4-Oxo-2-vinyl-2,3,3a,4,6,8a-hexahydro-furo[3,2-c]oxepin-3-yl)-(toluene-4-sulfonyl)-amino]-methyl}-2-vinyl-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyridine-4-carboxylic acid tert-butyl ester

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Technology Process of (2S,3S,3aS,7aR)-3-{[((2R,3S,3aS,8aS)-4-Oxo-2-vinyl-2,3,3a,4,6,8a-hexahydro-furo[3,2-c]oxepin-3-yl)-(toluene-4-sulfonyl)-amino]-methyl}-2-vinyl-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyridine-4-carboxylic acid tert-butyl ester

There total 6 articles about (2S,3S,3aS,7aR)-3-{[((2R,3S,3aS,8aS)-4-Oxo-2-vinyl-2,3,3a,4,6,8a-hexahydro-furo[3,2-c]oxepin-3-yl)-(toluene-4-sulfonyl)-amino]-methyl}-2-vinyl-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyridine-4-carboxylic 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: 82.0%

: 98-59-9
p-toluenesulfonyl chloride

: 792910-92-0
(2S,3S,3aS,7aR)-3-[((2R,3S,3aS,8aS)-4-Oxo-2-vinyl-2,3,3a,4,6,8a-hexahydro-furo[3,2-c]oxepin-3-ylamino)-methyl]-2-vinyl-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyridine-4-carboxylic acid tert-butyl ester

: 792910-93-1
(2S,3S,3aS,7aR)-3-{[((2R,3S,3aS,8aS)-4-Oxo-2-vinyl-2,3,3a,4,6,8a-hexahydro-furo[3,2-c]oxepin-3-yl)-(toluene-4-sulfonyl)-amino]-methyl}-2-vinyl-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyridine-4-carboxylic acid tert-butyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 48h;
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

: 792910-93-1
(2S,3S,3aS,7aR)-3-{[((2R,3S,3aS,8aS)-4-Oxo-2-vinyl-2,3,3a,4,6,8a-hexahydro-furo[3,2-c]oxepin-3-yl)-(toluene-4-sulfonyl)-amino]-methyl}-2-vinyl-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyridine-4-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 88 percent / NaH / dimethylformamide / 1.5 h

2.1: (N,N'-Mes₂imidazolidin-2-yl)Ru=CHPh(PCy₃)Cl₂ / CH₂Cl₂ / 0.75 h / 20 °C

2.2: 98 percent / CH₂Cl₂ / 20 °C

3.1: 62 percent / DIBAL / toluene / 0.17 h / -78 °C

4.1: 73 percent / pyridine; Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 °C

5.1: 90 percent / NaBH(OAc)3; AcOH / CH₂Cl₂ / 24 h

6.1: 82 percent / DMAP; Et₃N / CH₂Cl₂ / 48 h / 20 °C

With pyridine; dmap; sodium tris(acetoxy)borohydride; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; triethylamine; tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride; In dichloromethane; N,N-dimethyl-formamide; toluene; 4.1: Dess-Martin oxidation;
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

: 792910-93-1
(2S,3S,3aS,7aR)-3-{[((2R,3S,3aS,8aS)-4-Oxo-2-vinyl-2,3,3a,4,6,8a-hexahydro-furo[3,2-c]oxepin-3-yl)-(toluene-4-sulfonyl)-amino]-methyl}-2-vinyl-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyridine-4-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: (N,N'-Mes₂imidazolidin-2-yl)Ru=CHPh(PCy₃)Cl₂ / CH₂Cl₂ / 0.75 h / 20 °C

1.2: 98 percent / CH₂Cl₂ / 20 °C

2.1: 62 percent / DIBAL / toluene / 0.17 h / -78 °C

3.1: 73 percent / pyridine; Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 °C

4.1: 90 percent / NaBH(OAc)3; AcOH / CH₂Cl₂ / 24 h

5.1: 82 percent / DMAP; Et₃N / CH₂Cl₂ / 48 h / 20 °C

With pyridine; dmap; sodium tris(acetoxy)borohydride; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; triethylamine; tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride; In dichloromethane; toluene; 3.1: Dess-Martin oxidation;
DOI:10.1021/ol0484106