(3R,3aS,6aS,9R,9aS)-9-Hydroxy-3-(2-methyl-allyl)-6-(toluene-4-sulfonyl)-octahydro-7-oxa-1,6-diaza-cyclopenta[d]indene-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(3R,3aS,6aS,9R,9aS)-9-Hydroxy-3-(2-methyl-allyl)-6-(toluene-4-sulfonyl)-octahydro-7-oxa-1,6-diaza-cyclopenta[d]indene-1-carboxylic acid tert-butyl ester
CAS No.:217175-29-6
Molecular Formula:C₂₅H₃₆N₂O₆S
Molecular Weight:492.637
Hs Code.:

(3R,3aS,6aS,9R,9aS)-9-Hydroxy-3-(2-methyl-allyl)-6-(toluene-4-sulfonyl)-octahydro-7-oxa-1,6-diaza-cyclopenta[d]indene-1-carboxylic acid tert-butyl ester

Synonyms:(3R,3aS,6aS,9R,9aS)-9-Hydroxy-3-(2-methyl-allyl)-6-(toluene-4-sulfonyl)-octahydro-7-oxa-1,6-diaza-cyclopenta[d]indene-1-carboxylic acid tert-butyl ester

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Chemical Property of (3R,3aS,6aS,9R,9aS)-9-Hydroxy-3-(2-methyl-allyl)-6-(toluene-4-sulfonyl)-octahydro-7-oxa-1,6-diaza-cyclopenta[d]indene-1-carboxylic acid tert-butyl ester

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Technology Process of (3R,3aS,6aS,9R,9aS)-9-Hydroxy-3-(2-methyl-allyl)-6-(toluene-4-sulfonyl)-octahydro-7-oxa-1,6-diaza-cyclopenta[d]indene-1-carboxylic acid tert-butyl ester

There total 14 articles about (3R,3aS,6aS,9R,9aS)-9-Hydroxy-3-(2-methyl-allyl)-6-(toluene-4-sulfonyl)-octahydro-7-oxa-1,6-diaza-cyclopenta[d]indene-1-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: 78.0%

: 217175-28-5
(3R,4S,5S,9R)-9-Hydroxy-3-(2-methyl-allyl)-6-oxo-4-[2-(toluene-4-sulfonylamino)-ethyl]-7-oxa-1-aza-spiro[4.4]nonane-1-carboxylic acid tert-butyl ester

: 217175-29-6
(3R,3aS,6aS,9R,9aS)-9-Hydroxy-3-(2-methyl-allyl)-6-(toluene-4-sulfonyl)-octahydro-7-oxa-1,6-diaza-cyclopenta[d]indene-1-carboxylic acid tert-butyl ester

Guidance literature:: (3R,4S,5S,9R)-9-Hydroxy-3-(2-methyl-allyl)-6-oxo-4-[2-(toluene-4-sulfonylamino)-ethyl]-7-oxa-1-aza-spiro[4.4]nonane-1-carboxylic acid tert-butyl ester; With diisobutylaluminium hydride; In dichloromethane; at -78 ℃;

With hydrogenchloride;
DOI:10.1021/jo9817117

Reference yield:

: 18303-04-3
N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide

: 217175-29-6
(3R,3aS,6aS,9R,9aS)-9-Hydroxy-3-(2-methyl-allyl)-6-(toluene-4-sulfonyl)-octahydro-7-oxa-1,6-diaza-cyclopenta[d]indene-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: Ph₃P; DEAD / tetrahydrofuran

2.1: n-BuLi / diethyl ether

3.1: H₂ / Pd/CaCO₃/Pb / toluene

4.1: lithium hexamethyldisilazane / tetrahydrofuran; 1,2-dimethoxy-ethane / -78 °C

4.2: 71 percent / tetrahydrofuran; 1,2-dimethoxy-ethane / -78 °C

5.1: 69 percent / dimethylsulfoxide / 180 °C

6.1: 91 percent / Me₃Al / toluene

7.1: LHMDS / tetrahydrofuran / -78 °C

7.2: 79 percent / N,N-dimethylpropylene urea / tetrahydrofuran / -78 °C

8.1: 75 percent / aq. HCl / tetrahydrofuran

9.1: 98 percent / DMAP / acetonitrile

10.1: DIBALH / CH₂Cl₂ / -78 °C

11.1: NaCNBH₃ / acetic acid

12.1: TBAF / tetrahydrofuran

13.1: K₂CO₃ / methanol

14.1: DIBALH / CH₂Cl₂ / -78 °C

14.2: 78 percent / aq. HCl

With hydrogenchloride; dmap; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; trimethylaluminum; diisobutylaluminium hydride; sodium cyanoborohydride; potassium carbonate; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; Lindlar's catalyst; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; acetic acid; dimethyl sulfoxide; toluene; acetonitrile; 1.1: Alkylation / 2.1: Acylation / 3.1: Catalytic hydrogenation / 4.1: Metallation / 4.2: Michael addition / 5.1: Elimination / 6.1: Cyclization / 7.1: Metallation / 7.2: Alkylation / 8.1: Hydrolysis / 9.1: Acylation / 10.1: Reduction / 11.1: Reduction / 12.1: desilylation / 13.1: Cyclization / 14.1: Reduction / 14.2: Cyclization;
DOI:10.1021/jo9817117

Reference yield:

: 338463-00-6
N-(tert-butoxycarbonyl)-N-but-3-ynyl-4-methylbenzenesulfonamide

: 217175-29-6
(3R,3aS,6aS,9R,9aS)-9-Hydroxy-3-(2-methyl-allyl)-6-(toluene-4-sulfonyl)-octahydro-7-oxa-1,6-diaza-cyclopenta[d]indene-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: n-BuLi / diethyl ether

2.1: H₂ / Pd/CaCO₃/Pb / toluene

3.1: lithium hexamethyldisilazane / tetrahydrofuran; 1,2-dimethoxy-ethane / -78 °C

3.2: 71 percent / tetrahydrofuran; 1,2-dimethoxy-ethane / -78 °C

4.1: 69 percent / dimethylsulfoxide / 180 °C

5.1: 91 percent / Me₃Al / toluene

6.1: LHMDS / tetrahydrofuran / -78 °C

6.2: 79 percent / N,N-dimethylpropylene urea / tetrahydrofuran / -78 °C

7.1: 75 percent / aq. HCl / tetrahydrofuran

8.1: 98 percent / DMAP / acetonitrile

9.1: DIBALH / CH₂Cl₂ / -78 °C

10.1: NaCNBH₃ / acetic acid

11.1: TBAF / tetrahydrofuran

12.1: K₂CO₃ / methanol

13.1: DIBALH / CH₂Cl₂ / -78 °C

13.2: 78 percent / aq. HCl

With hydrogenchloride; dmap; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; trimethylaluminum; diisobutylaluminium hydride; sodium cyanoborohydride; potassium carbonate; lithium hexamethyldisilazane; Lindlar's catalyst; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; acetic acid; dimethyl sulfoxide; toluene; acetonitrile; 1.1: Acylation / 2.1: Catalytic hydrogenation / 3.1: Metallation / 3.2: Michael addition / 4.1: Elimination / 5.1: Cyclization / 6.1: Metallation / 6.2: Alkylation / 7.1: Hydrolysis / 8.1: Acylation / 9.1: Reduction / 10.1: Reduction / 11.1: desilylation / 12.1: Cyclization / 13.1: Reduction / 13.2: Cyclization;
DOI:10.1021/jo9817117