(-)-5-(benzyloxy)-8-(tert-butoxycarbonyl)-3a-methyl-3,3a,8,8a-tetrahydro-2H-furo<2,3-b>indol-2-one

Base Information

Chemical Name:(-)-5-(benzyloxy)-8-(tert-butoxycarbonyl)-3a-methyl-3,3a,8,8a-tetrahydro-2H-furo<2,3-b>indol-2-one
CAS No.:141661-45-2
Molecular Formula:C₂₃H₂₅NO₅
Molecular Weight:395.455
Hs Code.:

Synonyms:(-)-5-(benzyloxy)-8-(tert-butoxycarbonyl)-3a-methyl-3,3a,8,8a-tetrahydro-2H-furo<2,3-b>indol-2-one

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Chemical Property of (-)-5-(benzyloxy)-8-(tert-butoxycarbonyl)-3a-methyl-3,3a,8,8a-tetrahydro-2H-furo<2,3-b>indol-2-one

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Technology Process of (-)-5-(benzyloxy)-8-(tert-butoxycarbonyl)-3a-methyl-3,3a,8,8a-tetrahydro-2H-furo<2,3-b>indol-2-one

There total 23 articles about (-)-5-(benzyloxy)-8-(tert-butoxycarbonyl)-3a-methyl-3,3a,8,8a-tetrahydro-2H-furo<2,3-b>indol-2-one 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: 84.0%

: 141613-00-5
5-Benzyloxy-3,3-dichloro-3a-methyl-8a-methylsulfanyl-2-oxo-2,3,3a,8a-tetrahydro-furo[2,3-b]indole-8-carboxylic acid tert-butyl ester

: 141613-01-6,141661-45-2
5-(benzyloxy)-8-(tert-butoxycarbonyl)-3a-methyl-3,3a,8,8a-tetrahydro-2H-furo<2,3-b>indol-2-one

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 2h; Heating;
DOI:10.1021/ja00040a013

Reference yield:

: 21987-24-6
5-(benzyloxy)-3-methyl-1H-indole

: 141613-01-6,141661-45-2
(+)-5-(benzyloxy)-8-(tert-butoxycarbonyl)-3a-methyl-3,3a,8,8a-tetrahydro-2H-furo<2,3-b>indol-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / Et₃N, DMAP / tetrahydrofuran / 4 h / Ambient temperature

2: 1.) sec-BuLi / 1.) THF, hexane, -78 deg C, 5 min, 2.) THF, hexane, -78 deg C, 5 min

3: 70 percent / Zn, CuCl / tetrahydrofuran / 0.08 h

4: n-BuSnH, AIBN / toluene / 2 h / Heating

With dmap; n-butyl tin hydride; 2,2'-azobis(isobutyronitrile); sec.-butyllithium; triethylamine; copper(l) chloride; zinc; In tetrahydrofuran; toluene;
DOI:10.1021/ja00040a013

Reference yield:

: 21987-24-6
5-(benzyloxy)-3-methyl-1H-indole

: 141661-45-2
(-)-5-(benzyloxy)-8-(tert-butoxycarbonyl)-3a-methyl-3,3a,8,8a-tetrahydro-2H-furo<2,3-b>indol-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / Et₃N, DMAP / tetrahydrofuran / 4 h / Ambient temperature

2: 1.) sec-BuLi / 1.) THF, hexane, -78 deg C, 5 min, 2.) THF, hexane, -78 deg C, 5 min

3: 70 percent / Zn, CuCl / tetrahydrofuran / 0.08 h

4: n-BuSnH, AIBN / toluene / 2 h / Heating

With dmap; n-butyl tin hydride; 2,2'-azobis(isobutyronitrile); sec.-butyllithium; triethylamine; copper(l) chloride; zinc; In tetrahydrofuran; toluene;
DOI:10.1021/ja00040a013