tert-butyl (2S,3S,5R)-2-benzyl-3-methylsulfonyloxy-5-nonylpyrrolidine-1-carboxylate

Base Information

Chemical Name:tert-butyl (2S,3S,5R)-2-benzyl-3-methylsulfonyloxy-5-nonylpyrrolidine-1-carboxylate
CAS No.:888031-79-6
Molecular Formula:C₂₆H₄₃NO₅S
Molecular Weight:481.697
Hs Code.:

Synonyms:tert-butyl (2S,3S,5R)-2-benzyl-3-methylsulfonyloxy-5-nonylpyrrolidine-1-carboxylate

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Chemical Property of tert-butyl (2S,3S,5R)-2-benzyl-3-methylsulfonyloxy-5-nonylpyrrolidine-1-carboxylate

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Technology Process of tert-butyl (2S,3S,5R)-2-benzyl-3-methylsulfonyloxy-5-nonylpyrrolidine-1-carboxylate

There total 8 articles about tert-butyl (2S,3S,5R)-2-benzyl-3-methylsulfonyloxy-5-nonylpyrrolidine-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: 75.0%

: 888031-78-5
tert-butyl (1S,2S,4S)-(1-benzyl-2,4-dihydroxytridecyl)carbamate

: 124-63-0
methanesulfonyl chloride

: 888031-79-6
tert-butyl (2S,3S,5R)-2-benzyl-3-methylsulfonyloxy-5-nonylpyrrolidine-1-carboxylate

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 4h;
DOI:10.1002/ejoc.200500833

Reference yield:

: 888031-74-1
(1S)-allyldecyl acetate

: 888031-79-6
tert-butyl (2S,3S,5R)-2-benzyl-3-methylsulfonyloxy-5-nonylpyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 86 percent / 2,6-lutidine; OsO₄; NaIO₄ / dioxane; H₂O; propan-2-ol / 20 °C

2: La-(R)-BINOL / tetrahydrofuran / 60 h / -50 °C

3: 90 percent / hydrogen / Pd/C / methanol / 3 h

4: 80 percent / aq. HCl / 2 h / 20 °C

5: 91 percent / aq. sat. NaHCO₃ / ethyl acetate / 20 °C

6: 75 percent / triethylamine / CH₂Cl₂ / 4 h / 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; sodium periodate; osmium(VIII) oxide; lanthanum-(R)-(+)-binaphthol; hydrogen; sodium hydrogencarbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; isopropyl alcohol; 2: Shibasaki's asymmetric nitro-aldol reaction;
DOI:10.1002/ejoc.200500833

Reference yield:

: 888031-73-0
(3S)-3-acetoxydodecanal

: 888031-79-6
tert-butyl (2S,3S,5R)-2-benzyl-3-methylsulfonyloxy-5-nonylpyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: La-(R)-BINOL / tetrahydrofuran / 60 h / -50 °C

2: 90 percent / hydrogen / Pd/C / methanol / 3 h

3: 80 percent / aq. HCl / 2 h / 20 °C

4: 91 percent / aq. sat. NaHCO₃ / ethyl acetate / 20 °C

5: 75 percent / triethylamine / CH₂Cl₂ / 4 h / 20 °C

With hydrogenchloride; lanthanum-(R)-(+)-binaphthol; hydrogen; sodium hydrogencarbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; 1: Shibasaki's asymmetric nitro-aldol reaction;
DOI:10.1002/ejoc.200500833