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

Base Information

Chemical Name:(2S,3S,4R,5R)-1-benzyloxycarbonyl-2-(1',2'-dihydroxyethyl)-3,4-isopropylidenedioxy-5-methylpyrrolidine
CAS No.:362657-99-6
Molecular Formula:C₁₈H₂₅NO₆
Molecular Weight:351.4
Hs Code.:

Synonyms:(2S,3S,4R,5R)-1-benzyloxycarbonyl-2-(1',2'-dihydroxyethyl)-3,4-isopropylidenedioxy-5-methylpyrrolidine

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Chemical Property of (2S,3S,4R,5R)-1-benzyloxycarbonyl-2-(1',2'-dihydroxyethyl)-3,4-isopropylidenedioxy-5-methylpyrrolidine

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Technology Process of (2S,3S,4R,5R)-1-benzyloxycarbonyl-2-(1',2'-dihydroxyethyl)-3,4-isopropylidenedioxy-5-methylpyrrolidine

There total 5 articles about (2S,3S,4R,5R)-1-benzyloxycarbonyl-2-(1',2'-dihydroxyethyl)-3,4-isopropylidenedioxy-5-methylpyrrolidine 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: 79.0%

: 501-53-1,94274-21-2
benzyl chloroformate

: 362657-97-4
(2S,3S,4R,5R)-2-(1',2'-dihydroxyethyl)-3,4-isopropylidenedioxy-5-methylpyrrolidine

: 362657-99-6
(2S,3S,4R,5R)-1-benzyloxycarbonyl-2-(1',2'-dihydroxyethyl)-3,4-isopropylidenedioxy-5-methylpyrrolidine

Guidance literature:: With sodium carbonate; In 1,4-dioxane; water; at 20 ℃; for 2.5h;
DOI:10.1002/1099-0690(200107)2001:13<2547::AID-EJOC2547>3.0.CO;2-H

Reference yield:

: N-benzyl-3,4-O-isopropylidenedioxy-5-methyl-2-vinylpyrrolidine N-oxide, (1R,2S,3S,4R,5R)-isomer

: 362657-99-6
(2S,3S,4R,5R)-1-benzyloxycarbonyl-2-(1',2'-dihydroxyethyl)-3,4-isopropylidenedioxy-5-methylpyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1: 84 percent / activated Zn dust / acetic acid / 24 h / 20 °C

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

3: 100 percent / H₂ / Pearlman's catalyst / methanol / 72 h / 20 °C / 3000.3 Torr

4: 79 percent / Na₂CO₃ / dioxane; H₂O / 2.5 h / 20 °C

With osmium(VIII) oxide; hydrogen; sodium carbonate; 4-methylmorpholine N-oxide; zinc; palladium dihydroxide; In 1,4-dioxane; methanol; water; acetic acid; acetone; tert-butyl alcohol;
DOI:10.1002/1099-0690(200107)2001:13<2547::AID-EJOC2547>3.0.CO;2-H

Reference yield:

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

: 362657-99-6
(2S,3S,4R,5R)-1-benzyloxycarbonyl-2-(1',2'-dihydroxyethyl)-3,4-isopropylidenedioxy-5-methylpyrrolidine

Guidance literature:: Multi-step reaction with 3 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

With osmium(VIII) oxide; hydrogen; sodium carbonate; 4-methylmorpholine N-oxide; palladium dihydroxide; In 1,4-dioxane; methanol; water; acetone; tert-butyl alcohol;
DOI:10.1002/1099-0690(200107)2001:13<2547::AID-EJOC2547>3.0.CO;2-H