Acetic acid (S)-2-methyl-1-((3aR,3bR,6S,8aR)-8a-methyl-8-oxo-6-phenyl-2-thioxo-dihydro-[1,3]dioxolo[4',5':3,4]pyrrolo[1,2-c]oxazol-3b-yl)-propyl ester

Base Information

• Chemical Name: Acetic acid (S)-2-methyl-1-((3aR,3bR,6S,8aR)-8a-methyl-8-oxo-6-phenyl-2-thioxo-dihydro-[1,3]dioxolo[4',5':3,4]pyrrolo[1,2-c]oxazol-3b-yl)-propyl ester
• CAS No.: 154774-44-4
• Molecular Formula: C₂₀H₂₃NO₆S
• Molecular Weight: 405.472
• Mol file: 154774-44-4.mol

Synonyms:Acetic acid (S)-2-methyl-1-((3aR,3bR,6S,8aR)-8a-methyl-8-oxo-6-phenyl-2-thioxo-dihydro-[1,3]dioxolo[4',5':3,4]pyrrolo[1,2-c]oxazol-3b-yl)-propyl ester

Chemical Property of Acetic acid (S)-2-methyl-1-((3aR,3bR,6S,8aR)-8a-methyl-8-oxo-6-phenyl-2-thioxo-dihydro-[1,3]dioxolo[4',5':3,4]pyrrolo[1,2-c]oxazol-3b-yl)-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (S)-2-methyl-1-((3aR,3bR,6S,8aR)-8a-methyl-8-oxo-6-phenyl-2-thioxo-dihydro-[1,3]dioxolo[4',5':3,4]pyrrolo[1,2-c]oxazol-3b-yl)-propyl ester

There total 6 articles about Acetic acid (S)-2-methyl-1-((3aR,3bR,6S,8aR)-8a-methyl-8-oxo-6-phenyl-2-thioxo-dihydro-[1,3]dioxolo[4',5':3,4]pyrrolo[1,2-c]oxazol-3b-yl)-propyl 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: 91.0%

1,1'-Thiocarbonyldiimidazole (6160-65-2) + Acetic acid (S)-1-((3S,6R,7R,7aS)-6,7-dihydroxy-6-methyl-5-oxo-3-phenyl-dihydro-pyrrolo[1,2-c]oxazol-7a-yl)-2-methyl-propyl ester (154774-36-4) → Acetic acid (S)-2-methyl-1-((3aR,3bR,6S,8aR)-8a-methyl-8-oxo-6-phenyl-2-thioxo-dihydro-[1,3]dioxolo[4',5':3,4]pyrrolo[1,2-c]oxazol-3b-yl)-propyl ester (154774-44-4)

Guidance literature:

In tetrahydrofuran; Ambient temperature;

DOI:10.1021/ja00084a062

Reference yield:

(2S,5R)-2-phenyl-1-aza-3-oxabicyclo<3.3.0>octan-8-one (118918-76-6,1820583-17-2) → Acetic acid (S)-2-methyl-1-((3aR,3bR,6S,8aR)-8a-methyl-8-oxo-6-phenyl-2-thioxo-dihydro-[1,3]dioxolo[4',5':3,4]pyrrolo[1,2-c]oxazol-3b-yl)-propyl ester (154774-44-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) LDA, 2.) LDA, PhSeBr, 3.) O₃

2: 89 percent / 2,6-lutidine / CH₂Cl₂ / Ambient temperature

3: 55 percent / SnCl₄ / diethyl ether / -78 °C

4: 99 percent / pyridine / Ambient temperature

5: 87 percent / OsO₄, N-methylmorpholine N-oxide / acetone; H₂O / Ambient temperature

6: 91 percent / tetrahydrofuran / Ambient temperature

With pyridine; 2,6-dimethylpyridine; osmium(VIII) oxide; Phenylselenyl bromide; tin(IV) chloride; ozone; 4-methylmorpholine N-oxide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone;

DOI:10.1021/ja00084a062

Reference yield:

(3S,7aR)-6-Methyl-3-phenyl-1,7a-dihydro-pyrrolo[1,2-c]oxazol-5-one (154774-32-0) → Acetic acid (S)-2-methyl-1-((3aR,3bR,6S,8aR)-8a-methyl-8-oxo-6-phenyl-2-thioxo-dihydro-[1,3]dioxolo[4',5':3,4]pyrrolo[1,2-c]oxazol-3b-yl)-propyl ester (154774-44-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 89 percent / 2,6-lutidine / CH₂Cl₂ / Ambient temperature

2: 55 percent / SnCl₄ / diethyl ether / -78 °C

3: 99 percent / pyridine / Ambient temperature

4: 87 percent / OsO₄, N-methylmorpholine N-oxide / acetone; H₂O / Ambient temperature

5: 91 percent / tetrahydrofuran / Ambient temperature

With pyridine; 2,6-dimethylpyridine; osmium(VIII) oxide; tin(IV) chloride; 4-methylmorpholine N-oxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone;

DOI:10.1021/ja00084a062

upstream raw materials:

1,1'-Thiocarbonyldiimidazole

Acetic acid (S)-1-((3S,6R,7R,7aS)-6,7-dihydroxy-6-methyl-5-oxo-3-phenyl-dihydro-pyrrolo[1,2-c]oxazol-7a-yl)-2-methyl-propyl ester

(2S,5R)-2-phenyl-1-aza-3-oxabicyclo<3.3.0>octan-8-one

(3S,7aR)-6-Methyl-3-phenyl-1,7a-dihydro-pyrrolo[1,2-c]oxazol-5-one

Downstream raw materials:

(3R,4S,5R,1'S)-4-hydroxy-5-(1'-hydroxy-2'-methylpropyl)-3-methylpyrrolidin-2-one-5-carboxylic acid

Lactacystin