(1S,2R,4R)-(-)-N-[(1'-diphenylphosphinyl-(3'R)-3'-(4-nitrophenyl)-(2'R)-2'-aziridinyl)carbonyl]bornane-10,2-sultam

Base Information

• Chemical Name: (1S,2R,4R)-(-)-N-[(1'-diphenylphosphinyl-(3'R)-3'-(4-nitrophenyl)-(2'R)-2'-aziridinyl)carbonyl]bornane-10,2-sultam
• CAS No.: 185748-34-9
• Molecular Formula: C₃₁H₃₂N₃O₆PS
• Molecular Weight: 605.651

Synonyms:(1S,2R,4R)-(-)-N-[(1'-diphenylphosphinyl-(3'R)-3'-(4-nitrophenyl)-(2'R)-2'-aziridinyl)carbonyl]bornane-10,2-sultam

Chemical Property of (1S,2R,4R)-(-)-N-[(1'-diphenylphosphinyl-(3'R)-3'-(4-nitrophenyl)-(2'R)-2'-aziridinyl)carbonyl]bornane-10,2-sultam

Chemical Property:

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Technology Process of (1S,2R,4R)-(-)-N-[(1'-diphenylphosphinyl-(3'R)-3'-(4-nitrophenyl)-(2'R)-2'-aziridinyl)carbonyl]bornane-10,2-sultam

There total 2 articles about (1S,2R,4R)-(-)-N-[(1'-diphenylphosphinyl-(3'R)-3'-(4-nitrophenyl)-(2'R)-2'-aziridinyl)carbonyl]bornane-10,2-sultam 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: 77.0%

N-(4-nitrobenzylidene)-P,P-diphenylphosphinic amide (185748-28-1) + (3aS,6R,7aR)-1-(bromoacetyl)-8,8-dimethylhexahydro-3a,6-methano-2,1-benzothiazole 2,2-dioxide (185748-26-9) → (1S,2R,4R)-(-)-N-[(1'-diphenylphosphinyl-(3'R)-3'-(4-nitrophenyl)-(2'R)-2'-aziridinyl)carbonyl]bornane-10,2-sultam (185748-34-9)

Guidance literature:

(3aS,6R,7aR)-1-(bromoacetyl)-8,8-dimethylhexahydro-3a,6-methano-2,1-benzothiazole 2,2-dioxide; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

N-(4-nitrobenzylidene)-P,P-diphenylphosphinic amide; In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1016/j.tet.2006.01.068

Reference yield:

(2R)-bornane-10,2-sultam (94594-90-8,124224-04-0) → (1S,2R,4R)-(-)-N-[(1'-diphenylphosphinyl-(3'R)-3'-(4-nitrophenyl)-(2'R)-2'-aziridinyl)carbonyl]bornane-10,2-sultam (185748-34-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 71 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

2.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

2.2: 77 percent / tetrahydrofuran / 2 h / -78 °C

With n-butyllithium; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; 2.2: Darzens reaction;

DOI:10.1016/j.tet.2006.01.068

Reference yield: 60.0%

(1S,2R,4R)-(-)-N-[(1'-diphenylphosphinyl-(3'R)-3'-(4-nitrophenyl)-(2'R)-2'-aziridinyl)carbonyl]bornane-10,2-sultam (185748-34-9) → (2R,3R)-N-diphenylphosphinyl-2-carboxy-3-(4-nitrophenyl)aziridine

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1016/j.tet.2006.01.068

upstream raw materials:

N-(4-nitrobenzylidene)-P,P-diphenylphosphinic amide

(3aS,6R,7aR)-1-(bromoacetyl)-8,8-dimethylhexahydro-3a,6-methano-2,1-benzothiazole 2,2-dioxide

(2R)-bornane-10,2-sultam

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