(S)-4-Benzyloxyamino-5-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-methylene-5-oxo-pentanoic acid methyl ester

Base Information

• Chemical Name: (S)-4-Benzyloxyamino-5-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-methylene-5-oxo-pentanoic acid methyl ester
• CAS No.: 181826-59-5
• Molecular Formula: C₂₄H₃₂N₂O₆S
• Molecular Weight: 476.594

Synonyms:(S)-4-Benzyloxyamino-5-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-methylene-5-oxo-pentanoic acid methyl ester

Chemical Property of (S)-4-Benzyloxyamino-5-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-methylene-5-oxo-pentanoic acid methyl ester

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Technology Process of (S)-4-Benzyloxyamino-5-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-methylene-5-oxo-pentanoic acid methyl ester

There total 1 articles about (S)-4-Benzyloxyamino-5-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-methylene-5-oxo-pentanoic acid methyl ester 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:

methyl 2-(bromomethyl)propenoate (4224-69-5) + ((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-oxo-acetaldehyde O-benzyl-oxime (181826-43-7) → (R)-4-Benzyloxyamino-5-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2-methylene-5-oxo-pentanoic acid methyl ester + (S)-4-Benzyloxyamino-5-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2-methylene-5-oxo-pentanoic acid methyl ester (181826-59-5)

Guidance literature:

With ammonium chloride; zinc; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/0040-4039(96)01118-5

Reference yield: 100.0%

(S)-4-Benzyloxyamino-5-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2-methylene-5-oxo-pentanoic acid methyl ester (181826-59-5) → (S)-1-Benzyloxy-5-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-3-methylene-pyrrolidin-2-one (181826-69-7)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; Heating;

DOI:10.1016/0040-4039(96)01118-5

Reference yield:

(S)-4-Benzyloxyamino-5-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2-methylene-5-oxo-pentanoic acid methyl ester (181826-59-5) → (S)-(+)-methyl-4-methylene-5-oxopyrrolidine-2-carboxylate (182073-75-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / PTSA / toluene / Heating

2: Mo(CO)6 / acetonitrile; H₂O

3: Ti(OEt)4

With titanium(IV) tetraethanolate; hexacarbonyl molybdenum; toluene-4-sulfonic acid; In water; toluene; acetonitrile;

DOI:10.1016/0040-4039(96)01118-5

upstream raw materials:

methyl 2-(bromomethyl)propenoate

((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-oxo-acetaldehyde O-benzyl-oxime

Downstream raw materials:

(S)-1-Benzyloxy-5-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-3-methylene-pyrrolidin-2-one

(S)-(+)-methyl-4-methylene-5-oxopyrrolidine-2-carboxylate

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