(2S,5R)-1-benzyloxycarbonyl-2-(3-oxobutyl)-5-(6-heptenyl)pyrrolidine

Base Information

• Chemical Name: (2S,5R)-1-benzyloxycarbonyl-2-(3-oxobutyl)-5-(6-heptenyl)pyrrolidine
• CAS No.: 288270-27-9
• Molecular Formula: C₂₃H₃₃NO₃
• Molecular Weight: 371.52
• Mol file: 288270-27-9.mol

Synonyms:(2S,5R)-1-benzyloxycarbonyl-2-(3-oxobutyl)-5-(6-heptenyl)pyrrolidine

Chemical Property of (2S,5R)-1-benzyloxycarbonyl-2-(3-oxobutyl)-5-(6-heptenyl)pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R)-1-benzyloxycarbonyl-2-(3-oxobutyl)-5-(6-heptenyl)pyrrolidine

There total 13 articles about (2S,5R)-1-benzyloxycarbonyl-2-(3-oxobutyl)-5-(6-heptenyl)pyrrolidine 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: 75.0%

(2S,5R)-1-benzyloxycarbonyl-2-(3-oxo-1-butenyl)-5-(6-heptenyl)pyrrolidine (288270-23-5) → (2S,5R)-1-benzyloxycarbonyl-2-(3-oxobutyl)-5-(6-heptenyl)pyrrolidine (288270-27-9)

Guidance literature:

With copper(I) bromide; In tetrahydrofuran; 2-methyl-propan-1-ol; at -78 - -20 ℃; for 13h;

DOI:10.3987/COM-08-S(D)81

Reference yield:

1,5-Hexadien (592-42-7) → (2S,5R)-1-benzyloxycarbonyl-2-(3-oxobutyl)-5-(6-heptenyl)pyrrolidine (288270-27-9)

Guidance literature:

Multi-step reaction with 13 steps

1.1: AD-mix-β

2.1: PPTS

3.1: CH₃COBr; Et₃N

4.1: K₂CO₃; MeOH / diethyl ether

5.1: CuI

6.1: pyridine

7.1: NaN₃

8.1: LiAlH₄

9.1: K₂CO₃

10.1: Hg(OAc)2; NaBr / tetrahydrofuran

10.2: NaBR

10.3: NaBH₄; O₂ / dimethylformamide

11.1: (COCl)2; DMSO; Et₃N

12.1: iPr₂EtN; LiCl

13.1: Red-Al; CuBr

With pyridine; methanol; copper(l) iodide; lithium aluminium tetrahydride; sodium azide; oxalyl dichloride; Acetyl bromide; AD-mix-β; mercury(II) diacetate; pyridinium p-toluenesulfonate; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium bromide; lithium chloride; copper(I) bromide; In tetrahydrofuran; diethyl ether; 1.1: Sharpless asymmetric dihydroxylation / 2.1: orthoesterification / 3.1: Ring cleavage / 4.1: Cyclization / 5.1: Ring cleavage / 6.1: mesylation / 7.1: azidation / 8.1: Reduction / 9.1: carbamation / 10.1: oxymercuration / 10.2: anion exchange / 10.3: oxidative demercuration / 11.1: Oxidation / 12.1: Condensation / 13.1: Reduction;

DOI:10.1016/S0960-894X(00)00221-3

Reference yield:

(R)-1,2-dihydroxy-5-hexene (133494-68-5) → (2S,5R)-1-benzyloxycarbonyl-2-(3-oxobutyl)-5-(6-heptenyl)pyrrolidine (288270-27-9)

Guidance literature:

Multi-step reaction with 12 steps

1.1: PPTS

2.1: CH₃COBr; Et₃N

3.1: K₂CO₃; MeOH / diethyl ether

4.1: CuI

5.1: pyridine

6.1: NaN₃

7.1: LiAlH₄

8.1: K₂CO₃

9.1: Hg(OAc)2; NaBr / tetrahydrofuran

9.2: NaBR

9.3: NaBH₄; O₂ / dimethylformamide

10.1: (COCl)2; DMSO; Et₃N

11.1: iPr₂EtN; LiCl

12.1: Red-Al; CuBr

With pyridine; methanol; copper(l) iodide; lithium aluminium tetrahydride; sodium azide; oxalyl dichloride; Acetyl bromide; mercury(II) diacetate; pyridinium p-toluenesulfonate; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium bromide; lithium chloride; copper(I) bromide; In tetrahydrofuran; diethyl ether; 1.1: orthoesterification / 2.1: Ring cleavage / 3.1: Cyclization / 4.1: Ring cleavage / 5.1: mesylation / 6.1: azidation / 7.1: Reduction / 8.1: carbamation / 9.1: oxymercuration / 9.2: anion exchange / 9.3: oxidative demercuration / 10.1: Oxidation / 11.1: Condensation / 12.1: Reduction;

DOI:10.1016/S0960-894X(00)00221-3

upstream raw materials:

(2S,5R)-1-benzyloxycarbonyl-2-(3-oxo-1-butenyl)-5-(6-heptenyl)pyrrolidine

1,5-Hexadien

(R)-1,2-dihydroxy-5-hexene

(R)-2-(but-3-en-1-yl)oxirane

Downstream raw materials:

(2S,5R,6'S)-1-benzyloxycarbonyl-2-(3-oxobutyl)-5-(6',7'-dihydroxyheptyl)pyrrolidine

(2S,5R,6'R)-1-benzyloxycarbonyl-2-(3-oxobutyl)-5-(6',7'-dihydroxyheptyl)pyrrolidine

(2S,5R,6'R)-1-benzyloxycarbonyl-2-(3-oxobutyl)-5-(6'-hydroxy-7'-p-toluenesulfonyloxyheptyl)pyrrolidine