(2S,3S,4R,5R)-1-benzyl-3,4-isopropylidenedioxy-5-methyl-2-vinylpyrrolidine

Base Information

• Chemical Name: (2S,3S,4R,5R)-1-benzyl-3,4-isopropylidenedioxy-5-methyl-2-vinylpyrrolidine
• CAS No.: 362657-58-7
• Molecular Formula: C₁₇H₂₃NO₂
• Molecular Weight: 273.375
• Mol file: 362657-58-7.mol

Synonyms:(2S,3S,4R,5R)-1-benzyl-3,4-isopropylidenedioxy-5-methyl-2-vinylpyrrolidine

Chemical Property of (2S,3S,4R,5R)-1-benzyl-3,4-isopropylidenedioxy-5-methyl-2-vinylpyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,5R)-1-benzyl-3,4-isopropylidenedioxy-5-methyl-2-vinylpyrrolidine

There total 1 articles about (2S,3S,4R,5R)-1-benzyl-3,4-isopropylidenedioxy-5-methyl-2-vinylpyrrolidine 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: 84.0%

N-benzyl-3,4-O-isopropylidenedioxy-5-methyl-2-vinylpyrrolidine N-oxide, (1R,2S,3S,4R,5R)-isomer → (2S,3S,4R,5R)-1-benzyl-3,4-isopropylidenedioxy-5-methyl-2-vinylpyrrolidine (362657-58-7)

Guidance literature:

With zinc; In acetic acid; at 20 ℃; for 24h;

DOI:10.1002/1099-0690(200107)2001:13<2547::AID-EJOC2547>3.0.CO;2-H

Reference yield: 78.0%

(2S,3S,4R,5R)-1-benzyl-3,4-isopropylidenedioxy-5-methyl-2-vinylpyrrolidine (362657-58-7) → (2S,3S,4R,5R)-1-benzyl-3,4-dihydroxy-5-methyl-2-vinylpyrrolidine hydrochloride

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 3h;

DOI:10.1002/1099-0690(200107)2001:13<2547::AID-EJOC2547>3.0.CO;2-H

Reference yield:

(2S,3S,4R,5R)-1-benzyl-3,4-isopropylidenedioxy-5-methyl-2-vinylpyrrolidine (362657-58-7) → 2,5-(benzyloxycarbonylimino)-3,4-O-isopropylidene-2,5,6-trideoxy-D-allose (188242-67-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / N-methylmorpholine N-oxide; OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 108 h / 20 °C

2: 100 percent / H₂ / Pearlman's catalyst / methanol / 72 h / 20 °C / 3000.3 Torr

3: 79 percent / Na₂CO₃ / dioxane; H₂O / 2.5 h / 20 °C

4: 175 mg / K₂CO₃; lead tetraacetate / CH₂Cl₂ / 1 h / 20 °C

With lead(IV) acetate; osmium(VIII) oxide; hydrogen; sodium carbonate; potassium carbonate; 4-methylmorpholine N-oxide; palladium dihydroxide; In 1,4-dioxane; methanol; dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1002/1099-0690(200107)2001:13<2547::AID-EJOC2547>3.0.CO;2-H

Downstream raw materials:

(2S,3S,4R,5R)-3,4-dihydroxy-2-hydroxymethyl-5-methylpyrrolidine

(2S,3S,4R,5R)-1-benzyloxycarbonyl-2-hydroxymethyl-3,4-isopropylidenedioxy-5-methylpyrrolidine

2,5-(benzyloxycarbonylimino)-3,4-O-isopropylidene-2,5,6-trideoxy-D-allose

(2R,3S,4R,5R)-1-benzyloxycarbonyl-3,4-isopropylidenedioxy-5-methylproline methyl ester