(2S,4S)-2-[3-(N,N-dimethylamino)-1-hydroxypropyl]-N-(p-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidine

Base Information

Chemical Name:(2S,4S)-2-[3-(N,N-dimethylamino)-1-hydroxypropyl]-N-(p-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidine
CAS No.:194994-18-8
Molecular Formula:C₃₆H₃₉N₃O₅S
Molecular Weight:625.789
Hs Code.:

Synonyms:(2S,4S)-2-[3-(N,N-dimethylamino)-1-hydroxypropyl]-N-(p-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidine

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Chemical Property of (2S,4S)-2-[3-(N,N-dimethylamino)-1-hydroxypropyl]-N-(p-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidine

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Technology Process of (2S,4S)-2-[3-(N,N-dimethylamino)-1-hydroxypropyl]-N-(p-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidine

There total 8 articles about (2S,4S)-2-[3-(N,N-dimethylamino)-1-hydroxypropyl]-N-(p-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidine 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: 72.0%

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 194994-16-6
(2S,4S)-2-[1-hydroxy-3-(N-allyloxycarbonyl-N-methylamino)propyl]-N-(p-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidine

: 194994-18-8
(2S,4S)-2-[3-(N,N-dimethylamino)-1-hydroxypropyl]-N-(p-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidine

Guidance literature:: (2S,4S)-2-[1-hydroxy-3-(N-allyloxycarbonyl-N-methylamino)propyl]-N-(p-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidine; With bis-triphenylphosphine-palladium(II) chloride; tri-n-butyl-tin hydride; In dichloromethane; water; at 20 ℃; for 0.5h;

formaldehyd; With sodium tris(acetoxy)borohydride; acetic acid; In tetrahydrofuran; water; at 20 ℃; for 6h;
DOI:10.7164/antibiotics.50.598

Reference yield:

: 134441-71-7
(2S,4R)-1-boc-4-tert-butyldimethylsilylpyrrolidine-2-carbaldehyde

: 194994-18-8
(2S,4S)-2-[3-(N,N-dimethylamino)-1-hydroxypropyl]-N-(p-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidine

Guidance literature:: Multi-step reaction with 8 steps

1.1: 62 percent / hexamethyldisilazane; n-BuLi / tetrahydrofuran; hexane / 0.5 h / -70 °C

2.1: NaBH₄ / tetrahydrofuran; methanol / 0.5 h / 65 °C

3.1: 74 percent / NEt₃; DMAP / CH₂Cl₂ / 1 h / 20 °C

4.1: methanol / 8 h

4.2: NEt₃ / CH₂Cl₂

5.1: HCl / methanol / 10 h / 20 °C

5.2: 73 percent / NEt₃ / methanol; CH₂Cl₂ / 0.5 h / -10 °C

6.1: NEt₃ / CH₂Cl₂ / 0.5 h / 0 °C

6.2: 74 percent / dimethylformamide / 3 h / 70 °C

7.1: NaOH / methanol / 0.5 h / 20 °C

7.2: 73 percent / dimethylformamide / 10 h / 50 °C

8.1: (Ph₃P)2PdCl₂; n-Bu₃SnH / CH₂Cl₂; H₂O / 0.5 h / 20 °C

8.2: 72 percent / Ac(OH); NaBH(OAc)3 / tetrahydrofuran; H₂O / 6 h / 20 °C

With hydrogenchloride; dmap; bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; tri-n-butyl-tin hydride; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; hexane; dichloromethane; water; 1.1: Addition / 2.1: Reduction / 3.1: Tosylation / 4.1: Substitution / 4.2: Substitution / 5.1: Hydrolysis / 5.2: Substitution / 6.1: Substitution / 6.2: Substitution / 7.1: Hydrolysis / 7.2: Substitution / 8.1: deacylation / 8.2: Methylation;
DOI:10.7164/antibiotics.50.598

Reference yield:

: 149813-00-3
(3R,5S)-N-tert-butoxycarbonyl-3-tert-butyldimethylsilyloxy-5-((R)-1,3-dihydroxypropyl)pyrrolidine

: 194994-18-8
(2S,4S)-2-[3-(N,N-dimethylamino)-1-hydroxypropyl]-N-(p-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidine

Guidance literature:: Multi-step reaction with 6 steps

1.1: 74 percent / NEt₃; DMAP / CH₂Cl₂ / 1 h / 20 °C

2.1: methanol / 8 h

2.2: NEt₃ / CH₂Cl₂

3.1: HCl / methanol / 10 h / 20 °C

3.2: 73 percent / NEt₃ / methanol; CH₂Cl₂ / 0.5 h / -10 °C

4.1: NEt₃ / CH₂Cl₂ / 0.5 h / 0 °C

4.2: 74 percent / dimethylformamide / 3 h / 70 °C

5.1: NaOH / methanol / 0.5 h / 20 °C

5.2: 73 percent / dimethylformamide / 10 h / 50 °C

6.1: (Ph₃P)2PdCl₂; n-Bu₃SnH / CH₂Cl₂; H₂O / 0.5 h / 20 °C

6.2: 72 percent / Ac(OH); NaBH(OAc)3 / tetrahydrofuran; H₂O / 6 h / 20 °C

With hydrogenchloride; dmap; bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; tri-n-butyl-tin hydride; triethylamine; In methanol; dichloromethane; water; 1.1: Tosylation / 2.1: Substitution / 2.2: Substitution / 3.1: Hydrolysis / 3.2: Substitution / 4.1: Substitution / 4.2: Substitution / 5.1: Hydrolysis / 5.2: Substitution / 6.1: deacylation / 6.2: Methylation;
DOI:10.7164/antibiotics.50.598