1-benzyl 2-methyl (2S,3S,4S)-4-azido-3-hydroxypyrrolidine-1,2-dicarboxylate

Base Information

Chemical Name:1-benzyl 2-methyl (2S,3S,4S)-4-azido-3-hydroxypyrrolidine-1,2-dicarboxylate
CAS No.:1414607-51-4
Molecular Formula:C₁₄H₁₆N₄O₅
Molecular Weight:320.305
Hs Code.:

Synonyms:1-benzyl 2-methyl (2S,3S,4S)-4-azido-3-hydroxypyrrolidine-1,2-dicarboxylate

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Chemical Property of 1-benzyl 2-methyl (2S,3S,4S)-4-azido-3-hydroxypyrrolidine-1,2-dicarboxylate

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Technology Process of 1-benzyl 2-methyl (2S,3S,4S)-4-azido-3-hydroxypyrrolidine-1,2-dicarboxylate

There total 6 articles about 1-benzyl 2-methyl (2S,3S,4S)-4-azido-3-hydroxypyrrolidine-1,2-dicarboxylate 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: 95.0%

: 186581-53-3,908094-01-9,334-88-3
diazomethane

: 1414607-55-8
(3S,4S)-4-azido-1-[(benzyloxy)carbonyl]-3-hydroxy-L-proline

: 1414607-51-4
1-benzyl 2-methyl (2S,3S,4S)-4-azido-3-hydroxypyrrolidine-1,2-dicarboxylate

Guidance literature:: In tetrahydrofuran; diethyl ether; at -10 ℃; for 1h; Inert atmosphere;
DOI:10.1055/s-0032-1316612

Reference yield:

: 84730-22-3
(1S,3R,7R,8S,11R)-9-<(benzyloxy)carbonyl>-11-<(methylsulfonyl)oxy>-5,5-dimethyl-2,4,6-trioxa-9-azatricyclo<6.3.0.0^3,7>undecane

: 1414607-51-4
1-benzyl 2-methyl (2S,3S,4S)-4-azido-3-hydroxypyrrolidine-1,2-dicarboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: sodium azide / N,N-dimethyl-formamide / 24 h / 90 °C / Inert atmosphere

2: water; trifluoroacetic acid / 3.25 h / 0 - 25 °C

3: sodium periodate / acetone; water / 1 h / 25 °C

4: sodium dihydrogenphosphate; sodium chlorite; dihydrogen peroxide / water; acetonitrile / 2.5 h / -10 - 15 °C

5: tetrahydrofuran; diethyl ether / 1 h / -10 °C / Inert atmosphere

With sodium chlorite; sodium periodate; sodium dihydrogenphosphate; sodium azide; water; dihydrogen peroxide; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; water; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1055/s-0032-1316612

Reference yield:

: 1414607-58-1
3-[(benzyloxycarbonyl)amino]-3-deoxy-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose

: 1414607-51-4
1-benzyl 2-methyl (2S,3S,4S)-4-azido-3-hydroxypyrrolidine-1,2-dicarboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere

2: sodium azide / N,N-dimethyl-formamide / 24 h / 90 °C / Inert atmosphere

3: water; trifluoroacetic acid / 3.25 h / 0 - 25 °C

4: sodium periodate / acetone; water / 1 h / 25 °C

5: sodium dihydrogenphosphate; sodium chlorite; dihydrogen peroxide / water; acetonitrile / 2.5 h / -10 - 15 °C

6: tetrahydrofuran; diethyl ether / 1 h / -10 °C / Inert atmosphere

With sodium chlorite; sodium periodate; sodium dihydrogenphosphate; sodium azide; water; dihydrogen peroxide; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; water; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1055/s-0032-1316612