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

Base Information

Chemical Name:(2R,3S,4R,5R)-1-benzyloxycarbonyl-3,4-isopropylidenedioxy-5-methylproline methyl ester
CAS No.:362658-14-8
Molecular Formula:C₁₈H₂₃NO₆
Molecular Weight:349.384
Hs Code.:

Synonyms:

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

Chemical Property:

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

There total 8 articles about (2R,3S,4R,5R)-1-benzyloxycarbonyl-3,4-isopropylidenedioxy-5-methylproline methyl 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:

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

: 362658-14-8
(2R,3S,4R,5R)-1-benzyloxycarbonyl-3,4-isopropylidenedioxy-5-methylproline methyl ester

Guidance literature:: Multi-step reaction with 7 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

5: 175 mg / K₂CO₃; lead tetraacetate / CH₂Cl₂ / 1 h / 20 °C

6: 152 mg / aq. NaClO₂; aq. NaH₂PO₄ / 2-methyl-propan-2-ol; various solvent(s) / 5.5 h / 20 °C

7: 112 mg / methanol; diethyl ether

With lead(IV) acetate; sodium chlorite; sodium dihydrogenphosphate; osmium(VIII) oxide; hydrogen; sodium carbonate; potassium carbonate; 4-methylmorpholine N-oxide; zinc; palladium dihydroxide; In 1,4-dioxane; methanol; diethyl ether; dichloromethane; 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

: 362658-14-8
(2R,3S,4R,5R)-1-benzyloxycarbonyl-3,4-isopropylidenedioxy-5-methylproline methyl ester

Guidance literature:: Multi-step reaction with 6 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

5: 152 mg / aq. NaClO₂; aq. NaH₂PO₄ / 2-methyl-propan-2-ol; various solvent(s) / 5.5 h / 20 °C

6: 112 mg / methanol; diethyl ether

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

Reference yield:

: 362657-95-2
(2S,3S,4R,5R)-1-benzyl-2-(1',2'-dihydroxyethyl)-3,4-isopropylidenedioxy-5-methylpyrrolidine

: 362658-14-8
(2R,3S,4R,5R)-1-benzyloxycarbonyl-3,4-isopropylidenedioxy-5-methylproline methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / H₂ / Pearlman's catalyst / methanol / 72 h / 20 °C / 3000.3 Torr

2: 79 percent / Na₂CO₃ / dioxane; H₂O / 2.5 h / 20 °C

3: 175 mg / K₂CO₃; lead tetraacetate / CH₂Cl₂ / 1 h / 20 °C

4: 152 mg / aq. NaClO₂; aq. NaH₂PO₄ / 2-methyl-propan-2-ol; various solvent(s) / 5.5 h / 20 °C

5: 112 mg / methanol; diethyl ether

With lead(IV) acetate; sodium chlorite; sodium dihydrogenphosphate; hydrogen; sodium carbonate; potassium carbonate; palladium dihydroxide; In 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; tert-butyl alcohol;
DOI:10.1002/1099-0690(200107)2001:13<2547::AID-EJOC2547>3.0.CO;2-H