(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

Base Information

• Chemical Name: (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
• CAS No.: 181826-69-7
• Molecular Formula: C₂₃H₂₈N₂O₅S
• Molecular Weight: 444.552

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Technology Process of (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

There total 6 articles about (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 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: 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:

O-benzyl tert-butyl glyoxylate oxime ether (203127-16-6) → (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:

Multi-step reaction with 4 steps

1: 1.) (R,R)-2,2'-methylene-bis(4-phenyloxazoline), n-BuLi / 1.) THF, hexane, -78 deg C to 0 deg C, 15 min, 2.) THF, -78 deg C, 0.5 h

2: TFA / CH₂Cl₂

3: PTSA / toluene / Heating

With n-butyllithium; toluene-4-sulfonic acid; trifluoroacetic acid; 2,2'-methylenebis[(4R)-4-phenyl-4,5-dihydro-2-oxazole]; In dichloromethane; toluene;

DOI:10.1016/S0040-4039(96)02112-0

Reference yield:

N-benzyloxy-4-methylene-(S)-glutamic acid (186749-79-1) → (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:

Multi-step reaction with 2 steps

1: PTSA / toluene / Heating

With toluene-4-sulfonic acid; In toluene;

DOI:10.1016/S0040-4039(96)02112-0

upstream raw materials:

(S)-1-Benzyloxy-4-methylene-5-oxo-pyrrolidine-2-carboxylic acid

(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

O-benzyl tert-butyl glyoxylate oxime ether

N-benzyloxy-4-methylene-(S)-glutamic acid

Downstream raw materials:

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

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