5-[(S)-4-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-[1-iodo-meth-(Z)-ylidene]-4-methyl-pyrrolidin-(2Z)-ylidenemethyl]-4-tert-butoxymethyl-4-methyl-3,4-dihydro-pyrrol-2-one

Base Information

• Chemical Name: 5-[(S)-4-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-[1-iodo-meth-(Z)-ylidene]-4-methyl-pyrrolidin-(2Z)-ylidenemethyl]-4-tert-butoxymethyl-4-methyl-3,4-dihydro-pyrrol-2-one
• CAS No.: 223664-01-5
• Molecular Formula: C₃₇H₄₇IN₂O₅
• Molecular Weight: 726.695
• Mol file: 223664-01-5.mol

Synonyms:5-[(S)-4-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-[1-iodo-meth-(Z)-ylidene]-4-methyl-pyrrolidin-(2Z)-ylidenemethyl]-4-tert-butoxymethyl-4-methyl-3,4-dihydro-pyrrol-2-one

Chemical Property of 5-[(S)-4-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-[1-iodo-meth-(Z)-ylidene]-4-methyl-pyrrolidin-(2Z)-ylidenemethyl]-4-tert-butoxymethyl-4-methyl-3,4-dihydro-pyrrol-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-[(S)-4-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-[1-iodo-meth-(Z)-ylidene]-4-methyl-pyrrolidin-(2Z)-ylidenemethyl]-4-tert-butoxymethyl-4-methyl-3,4-dihydro-pyrrol-2-one

There total 11 articles about 5-[(S)-4-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-[1-iodo-meth-(Z)-ylidene]-4-methyl-pyrrolidin-(2Z)-ylidenemethyl]-4-tert-butoxymethyl-4-methyl-3,4-dihydro-pyrrol-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: 80.0%

(S)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-[1-(3-tert-butoxymethyl-3-methyl-5-oxo-4,5-dihydro-3H-pyrrol-2-yl)-meth-(Z)-ylidene]-2,3-dimethyl-pyrrolidine-2-carbonitrile (223663-93-2) → 5-[(S)-4-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-[1-iodo-meth-(Z)-ylidene]-4-methyl-pyrrolidin-(2Z)-ylidenemethyl]-4-tert-butoxymethyl-4-methyl-3,4-dihydro-pyrrol-2-one (223664-01-5)

Guidance literature:

(S)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-[1-(3-tert-butoxymethyl-3-methyl-5-oxo-4,5-dihydro-3H-pyrrol-2-yl)-meth-(Z)-ylidene]-2,3-dimethyl-pyrrolidine-2-carbonitrile; With potassium tert-butylate; In tert-butyl alcohol; at 85 ℃;

With iodine; potassium carbonate; In dichloromethane; at 0 ℃;

DOI:10.1002/(SICI)1521-3773(19990401)38:7<923::AID-ANIE923>3.0.CO;2-7

Reference yield:

4-tert-Butoxymethyl-4-methyl-5-methylene-pyrrolidin-2-one (197068-20-5) → 5-[(S)-4-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-[1-iodo-meth-(Z)-ylidene]-4-methyl-pyrrolidin-(2Z)-ylidenemethyl]-4-tert-butoxymethyl-4-methyl-3,4-dihydro-pyrrol-2-one (223664-01-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N-iodosuccinimide; t-BuOK / 2-methyl-propan-2-ol; benzene / 20 °C

2.1: (EtO)3P / xylene / 125 °C

3.1: t-BuOK / 2-methyl-propan-2-ol / 85 °C

3.2: 80 percent / I₂; K₂CO₃ / CH₂Cl₂ / 0 °C

With N-iodo-succinimide; potassium tert-butylate; triethyl phosphite; In xylene; tert-butyl alcohol; benzene; 1.1: Iodination / 2.1: Substitution / 3.1: Metallation / 3.2: Iodination;

DOI:10.1002/(SICI)1521-3773(19990401)38:7<923::AID-ANIE923>3.0.CO;2-7

Reference yield:

5-tert-butoxymethyl-3-methyl-dihydro-furan-2-one → 5-[(S)-4-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-[1-iodo-meth-(Z)-ylidene]-4-methyl-pyrrolidin-(2Z)-ylidenemethyl]-4-tert-butoxymethyl-4-methyl-3,4-dihydro-pyrrol-2-one (223664-01-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: LDA / tetrahydrofuran / -78 °C

1.2: hexamethylphosphoric acid triamide

2.1: TMSOTf / CH₂Cl₂; tetrahydrofuran / 0 °C

3.1: TFA / CH₂Cl₂ / 20 °C

4.1: tetrahydrofuran / -78 °C

5.1: 70 percent

6.1: 70 percent / methanol / 60 °C

7.1: 98 percent / Lawesson's reagent / toluene / 80 °C

8.1: (EtO)3P / xylene / 125 °C

9.1: t-BuOK / 2-methyl-propan-2-ol / 85 °C

9.2: 80 percent / I₂; K₂CO₃ / CH₂Cl₂ / 0 °C

With Lawessons reagent; trimethylsilyl trifluoromethanesulfonate; potassium tert-butylate; trifluoroacetic acid; lithium diisopropyl amide; triethyl phosphite; In tetrahydrofuran; methanol; dichloromethane; toluene; xylene; tert-butyl alcohol; 1.1: Metallation / 1.2: Etherification / 2.1: Substitution / 3.1: Substitution / 4.1: Methylation / 6.1: Addition / 7.1: Substitution / 8.1: Substitution / 9.1: Metallation / 9.2: Iodination;

DOI:10.1002/(SICI)1521-3773(19990401)38:7<923::AID-ANIE923>3.0.CO;2-7

upstream raw materials:

(S)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-[1-(3-tert-butoxymethyl-3-methyl-5-oxo-4,5-dihydro-3H-pyrrol-2-yl)-meth-(Z)-ylidene]-2,3-dimethyl-pyrrolidine-2-carbonitrile

4-tert-Butoxymethyl-4-methyl-5-methylene-pyrrolidin-2-one

(5-tert-butoxymethyl-3-methyl-4,5-dihydro-furan-2-yloxy)-tert-butyl-dimethyl-silane

(S)-4-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-4-methyl-5-methylene-pyrrolidin-2-one