(3S,5R)-5-azidomethyl-3-benzyloxymethoxy-N-methoxycarbonylmethyl-2-pyrrolidinone

Base Information

Chemical Name:(3S,5R)-5-azidomethyl-3-benzyloxymethoxy-N-methoxycarbonylmethyl-2-pyrrolidinone
CAS No.:329005-71-2
Molecular Formula:C₁₆H₂₀N₄O₅
Molecular Weight:348.359
Hs Code.:

Synonyms:(3S,5R)-5-azidomethyl-3-benzyloxymethoxy-N-methoxycarbonylmethyl-2-pyrrolidinone

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Chemical Property of (3S,5R)-5-azidomethyl-3-benzyloxymethoxy-N-methoxycarbonylmethyl-2-pyrrolidinone

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Technology Process of (3S,5R)-5-azidomethyl-3-benzyloxymethoxy-N-methoxycarbonylmethyl-2-pyrrolidinone

There total 7 articles about (3S,5R)-5-azidomethyl-3-benzyloxymethoxy-N-methoxycarbonylmethyl-2-pyrrolidinone 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: 98.0%

: 329005-70-1
(3S,5R)-3-benzyloxymethoxy-N-methoxycarbonylmethyl-5-[methylsulfonylmethyl]-2-pyrrolidinone

: 329005-71-2
(3S,5R)-5-azidomethyl-3-benzyloxymethoxy-N-methoxycarbonylmethyl-2-pyrrolidinone

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 80 ℃;
DOI:10.1021/jo001000k

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 329005-71-2
(3S,5R)-5-azidomethyl-3-benzyloxymethoxy-N-methoxycarbonylmethyl-2-pyrrolidinone

Guidance literature:: Multi-step reaction with 6 steps

1: 94 percent / DIEA / CH₂Cl₂ / 20 °C

2: 59 percent / TFA / CH₂Cl₂ / 0.13 h / 0 °C

3: 100 percent / NaH / tetrahydrofuran / 0 - 20 °C

4: 99 percent / Et₃N*3HF / tetrahydrofuran / 10 h / 50 °C

5: 86 percent / Et₃N / CH₂Cl₂ / 2.25 h / 0 °C

6: 98 percent / NaN₃ / dimethylformamide / 80 °C

With sodium azide; sodium hydride; triethylamine tris(hydrogen fluoride); triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo001000k

Reference yield:

: 329005-69-8
(3S,5R)-3-benzyloxymethoxy-5-hydroxymethyl-N-[methoxycarbonylmethyl]-2-pyrrolidinone

: 329005-71-2
(3S,5R)-5-azidomethyl-3-benzyloxymethoxy-N-methoxycarbonylmethyl-2-pyrrolidinone

Guidance literature:: Multi-step reaction with 2 steps

1: 86 percent / Et₃N / CH₂Cl₂ / 2.25 h / 0 °C

2: 98 percent / NaN₃ / dimethylformamide / 80 °C

With sodium azide; triethylamine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo001000k