(2S,3R,5R)-3-{(tert-butyldimethylsilyl)oxy}-2-[{(tert-butyldimethylsilyl)oxy}methyl]-1-{(2-nitrophenyl)sulfonyl}-5-vinylpyrrolidine

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Chemical Name:(2S,3R,5R)-3-{(tert-butyldimethylsilyl)oxy}-2-[{(tert-butyldimethylsilyl)oxy}methyl]-1-{(2-nitrophenyl)sulfonyl}-5-vinylpyrrolidine
CAS No.:1449498-67-2
Molecular Formula:C₂₅H₄₄N₂O₆SSi₂
Molecular Weight:556.871
Hs Code.:

Synonyms:(2S,3R,5R)-3-{(tert-butyldimethylsilyl)oxy}-2-[{(tert-butyldimethylsilyl)oxy}methyl]-1-{(2-nitrophenyl)sulfonyl}-5-vinylpyrrolidine

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Chemical Property of (2S,3R,5R)-3-{(tert-butyldimethylsilyl)oxy}-2-[{(tert-butyldimethylsilyl)oxy}methyl]-1-{(2-nitrophenyl)sulfonyl}-5-vinylpyrrolidine

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Technology Process of (2S,3R,5R)-3-{(tert-butyldimethylsilyl)oxy}-2-[{(tert-butyldimethylsilyl)oxy}methyl]-1-{(2-nitrophenyl)sulfonyl}-5-vinylpyrrolidine

There total 8 articles about (2S,3R,5R)-3-{(tert-butyldimethylsilyl)oxy}-2-[{(tert-butyldimethylsilyl)oxy}methyl]-1-{(2-nitrophenyl)sulfonyl}-5-vinylpyrrolidine 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: 99.0%

: 1449498-83-2
(2Z,5R,6S)-5,7-bis{(tert-butyldimethylsilyl)oxy}-6-(2-nitrophenylsulfonamido)hept-2-en-1-yl methyl carbonate

: 1449498-67-2
(2S,3R,5R)-3-{(tert-butyldimethylsilyl)oxy}-2-[{(tert-butyldimethylsilyl)oxy}methyl]-1-{(2-nitrophenyl)sulfonyl}-5-vinylpyrrolidine

Guidance literature:: With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; In tetrahydrofuran; at 20 - 40 ℃; for 12h; diastereoselective reaction; Inert atmosphere;
DOI:10.1039/c3ob42229a

Reference yield: 88.0%

: (5R,6S)-5,7-bis{(tert-butyldimethylsilyl)oxy}-6-(2-nitrophenylsulfonamido)hept-2-en-1-yl methyl carbonate

: 1449498-67-2
(2S,3R,5R)-3-{(tert-butyldimethylsilyl)oxy}-2-[{(tert-butyldimethylsilyl)oxy}methyl]-1-{(2-nitrophenyl)sulfonyl}-5-vinylpyrrolidine

: 1449498-68-3
(2S,3R,5S)-3-{(tert-butyldimethylsilyl)oxy}-2-[{(tert-butyldimethylsilyl)oxy}methyl]-1-{(2-nitrophenyl)sulfonyl}-5-vinylpyrrolidine

Guidance literature:: With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine; In tetrahydrofuran; at 40 ℃; for 15h; Time; diastereoselective reaction;
DOI:10.3987/COM-12-S(N)99

Reference yield:

: 1301261-30-2
C₂₀H₃₉NO₄Si

: 1449498-67-2
(2S,3R,5R)-3-{(tert-butyldimethylsilyl)oxy}-2-[{(tert-butyldimethylsilyl)oxy}methyl]-1-{(2-nitrophenyl)sulfonyl}-5-vinylpyrrolidine

Guidance literature:: Multi-step reaction with 7 steps

1.1: ozone / dichloromethane / 1 h / -78 °C / Inert atmosphere

1.2: 18 h / -78 - 20 °C / Inert atmosphere

2.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

2.2: 0.5 h / -78 °C / Inert atmosphere

2.3: 1 h / -78 °C / Inert atmosphere

3.1: dmap; pyridine / dichloromethane / 13 h / 20 °C / Inert atmosphere

4.1: trifluoroacetic acid / dichloromethane / 1 h / 0 °C / Inert atmosphere

5.1: 1H-imidazole / dichloromethane / 15 h / 0 - 20 °C / Inert atmosphere

6.1: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

7.1: bis(1,5-cyclooctadiene)diiridium(I) dichloride; (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine / tetrahydrofuran / 12 h / 20 - 40 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; sodium hydride; ozone; triethylamine; trifluoroacetic acid; (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; In tetrahydrofuran; dichloromethane; mineral oil; 2.1: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1039/c3ob42229a