(2S,3R,4S)-N-benzyloxycarbonyl-3,4-dihydroxyproline-3,4-isopropylidene acetal methyl ester

Base Information

Chemical Name:(2S,3R,4S)-N-benzyloxycarbonyl-3,4-dihydroxyproline-3,4-isopropylidene acetal methyl ester
CAS No.:111193-62-5
Molecular Formula:C₁₇H₂₁NO₆
Molecular Weight:335.357
Hs Code.:

Synonyms:(2S,3R,4S)-N-benzyloxycarbonyl-3,4-dihydroxyproline-3,4-isopropylidene acetal methyl ester

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Chemical Property of (2S,3R,4S)-N-benzyloxycarbonyl-3,4-dihydroxyproline-3,4-isopropylidene acetal methyl ester

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Technology Process of (2S,3R,4S)-N-benzyloxycarbonyl-3,4-dihydroxyproline-3,4-isopropylidene acetal methyl ester

There total 8 articles about (2S,3R,4S)-N-benzyloxycarbonyl-3,4-dihydroxyproline-3,4-isopropylidene acetal 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: 89.0%

: methyl 1-benzyloxycarbonyl-3(RS),4(SR)-dihydroxy-2(S)-pyrrolidinylcarboxylate

: 77-76-9
2,2-dimethoxy-propane

: 111193-62-5
(2S,3R,4S)-N-benzyloxycarbonyl-3,4-dihydroxyproline-3,4-isopropylidene acetal methyl ester

: 111193-64-7
methyl 1-benzyloxycarbonyl-(3S,4R)-isopropylidenedioxy-(2S)-pyrrolidinylcarboxylate

Guidance literature:: With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1016/j.bmc.2005.11.058

Reference yield:

: 5211-24-5
(2S)-2,5-dihydro-1H-pyrrole-1,2-dicarboxylic acid 2-methyl 1-(phenylmethyl) ester

: 111193-62-5
(2S,3R,4S)-N-benzyloxycarbonyl-3,4-dihydroxyproline-3,4-isopropylidene acetal methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / N-methylmorpholine N-oxide; H₂O / OsO₄ / acetone / 24 h / 20 °C

2: 89 percent / p-TsOH*H₂O / CH₂Cl₂ / 1 h / 20 °C

With water; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; osmium(VIII) oxide; In dichloromethane; acetone;
DOI:10.1016/j.bmc.2005.11.058

Reference yield:

: 64187-48-0
methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate

: 111193-62-5
(2S,3R,4S)-N-benzyloxycarbonyl-3,4-dihydroxyproline-3,4-isopropylidene acetal methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / methyl triflate; N-methylimidazole / tetrahydrofuran / 0 - 20 °C

2: 82 percent / NaBH₄ / methanol / 5 h / Heating

3: 74 percent / H₂O₂; pyridine / CH₂Cl₂ / 0 - 20 °C

4: 95 percent / N-methylmorpholine N-oxide; H₂O / OsO₄ / acetone / 24 h / 20 °C

5: 89 percent / p-TsOH*H₂O / CH₂Cl₂ / 1 h / 20 °C

With pyridine; 1-methyl-1H-imidazole; sodium tetrahydroborate; water; dihydrogen peroxide; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; methyl trifluoromethanesulfonate; osmium(VIII) oxide; In tetrahydrofuran; methanol; dichloromethane; acetone;
DOI:10.1016/j.bmc.2005.11.058