(2S,3S,3aS,6S,7aS)-tert-butyl 3,3a-bis(3-(tert-butyldimethylsilyloxy)propyl)-6-methyl-2-((phenoxycarbonothioyloxy)methyl)-2,3,3a,6,7,7a-hexahydro-1H-indole-1-carboxylate

Base Information

Chemical Name:(2S,3S,3aS,6S,7aS)-tert-butyl 3,3a-bis(3-(tert-butyldimethylsilyloxy)propyl)-6-methyl-2-((phenoxycarbonothioyloxy)methyl)-2,3,3a,6,7,7a-hexahydro-1H-indole-1-carboxylate
CAS No.:1428243-86-0
Molecular Formula:C₄₀H₆₉NO₆SSi₂
Molecular Weight:748.228
Hs Code.:

(2S,3S,3aS,6S,7aS)-tert-butyl 3,3a-bis(3-(tert-butyldimethylsilyloxy)propyl)-6-methyl-2-((phenoxycarbonothioyloxy)methyl)-2,3,3a,6,7,7a-hexahydro-1H-indole-1-carboxylate

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Chemical Property of (2S,3S,3aS,6S,7aS)-tert-butyl 3,3a-bis(3-(tert-butyldimethylsilyloxy)propyl)-6-methyl-2-((phenoxycarbonothioyloxy)methyl)-2,3,3a,6,7,7a-hexahydro-1H-indole-1-carboxylate

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Technology Process of (2S,3S,3aS,6S,7aS)-tert-butyl 3,3a-bis(3-(tert-butyldimethylsilyloxy)propyl)-6-methyl-2-((phenoxycarbonothioyloxy)methyl)-2,3,3a,6,7,7a-hexahydro-1H-indole-1-carboxylate

There total 8 articles about (2S,3S,3aS,6S,7aS)-tert-butyl 3,3a-bis(3-(tert-butyldimethylsilyloxy)propyl)-6-methyl-2-((phenoxycarbonothioyloxy)methyl)-2,3,3a,6,7,7a-hexahydro-1H-indole-1-carboxylate 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:

: 1428243-85-9
(2S,3S,3aS,6S,7aS)-tert-butyl 3,3a-bis(3-(tert-butyldimethylsilyloxy)propyl)-2-(hydroxymethyl)-6-methyl-2,3,3a,6,7,7a-hexahydro-1H-indole-1-carboxylate

: 1005-56-7
phenylcarbonochloridothioate

: 1428243-86-0
(2S,3S,3aS,6S,7aS)-tert-butyl 3,3a-bis(3-(tert-butyldimethylsilyloxy)propyl)-6-methyl-2-((phenoxycarbonothioyloxy)methyl)-2,3,3a,6,7,7a-hexahydro-1H-indole-1-carboxylate

Guidance literature:: With dmap; In acetonitrile; at 50 ℃; for 2h; Inert atmosphere;
DOI:10.1002/anie.201206863

Reference yield:

: 1428243-80-4
(S,E)-10-(tert-butyldimethylsilyloxy)-6-(3-(tert-butyldimethylsilyloxy)propyl)-1-hydroxy-3-methyldec-6-en-5-one

: 1428243-86-0
(2S,3S,3aS,6S,7aS)-tert-butyl 3,3a-bis(3-(tert-butyldimethylsilyloxy)propyl)-6-methyl-2-((phenoxycarbonothioyloxy)methyl)-2,3,3a,6,7,7a-hexahydro-1H-indole-1-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve

2.1: toluene / 12.5 h / 20 °C / Inert atmosphere; Reflux

3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 2 h / 20 °C / Inert atmosphere

3.2: 0.5 h / 20 °C / Inert atmosphere

4.1: 20% palladium hydroxide-activated charcoal; hydrogen; water / ethyl acetate / 12 h / 20 °C

5.1: toluene / 1 h / 20 °C / Inert atmosphere

6.1: N,N,N,N,-tetramethylethylenediamine; monochloromethanesulfonyl chloride / toluene / 3 h / 20 °C / Inert atmosphere

6.2: 3 h / Inert atmosphere; Reflux

7.1: dmap / acetonitrile / 2 h / 50 °C / Inert atmosphere

With dmap; tetrapropylammonium perruthennate; N,N,N,N,-tetramethylethylenediamine; monochloromethanesulfonyl chloride; 20% palladium hydroxide-activated charcoal; water; hydrogen; 4-methylmorpholine N-oxide; sodium bis(2-methoxyethoxy)aluminium dihydride; In dichloromethane; ethyl acetate; toluene; acetonitrile;
DOI:10.1002/anie.201206863

Reference yield:

: 1428243-81-5
(S,E)-10-(tert-butyldimethylsilyloxy)-6-(3-(tert-butyldimethylsilyloxy)propyl)-3-methyl-5-oxodec-6-enal

: 1428243-86-0
(2S,3S,3aS,6S,7aS)-tert-butyl 3,3a-bis(3-(tert-butyldimethylsilyloxy)propyl)-6-methyl-2-((phenoxycarbonothioyloxy)methyl)-2,3,3a,6,7,7a-hexahydro-1H-indole-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: toluene / 12.5 h / 20 °C / Inert atmosphere; Reflux

2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 2 h / 20 °C / Inert atmosphere

2.2: 0.5 h / 20 °C / Inert atmosphere

3.1: 20% palladium hydroxide-activated charcoal; hydrogen; water / ethyl acetate / 12 h / 20 °C

4.1: toluene / 1 h / 20 °C / Inert atmosphere

5.1: N,N,N,N,-tetramethylethylenediamine; monochloromethanesulfonyl chloride / toluene / 3 h / 20 °C / Inert atmosphere

5.2: 3 h / Inert atmosphere; Reflux

6.1: dmap / acetonitrile / 2 h / 50 °C / Inert atmosphere

With dmap; N,N,N,N,-tetramethylethylenediamine; monochloromethanesulfonyl chloride; 20% palladium hydroxide-activated charcoal; water; hydrogen; sodium bis(2-methoxyethoxy)aluminium dihydride; In ethyl acetate; toluene; acetonitrile;
DOI:10.1002/anie.201206863