benzyl (2S,3S)-3-hexyl-2-<(R)-2-hydroxytridecyl>-4-oxoazetidine-1-acetate

Base Information

Chemical Name:benzyl (2S,3S)-3-hexyl-2-<(R)-2-hydroxytridecyl>-4-oxoazetidine-1-acetate
CAS No.:160452-49-3
Molecular Formula:C₃₁H₅₁NO₄
Molecular Weight:501.75
Hs Code.:

Synonyms:benzyl (2S,3S)-3-hexyl-2-<(R)-2-hydroxytridecyl>-4-oxoazetidine-1-acetate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of benzyl (2S,3S)-3-hexyl-2-<(R)-2-hydroxytridecyl>-4-oxoazetidine-1-acetate

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Technology Process of benzyl (2S,3S)-3-hexyl-2-<(R)-2-hydroxytridecyl>-4-oxoazetidine-1-acetate

There total 16 articles about benzyl (2S,3S)-3-hexyl-2-<(R)-2-hydroxytridecyl>-4-oxoazetidine-1-acetate 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: 91.9%

: 160452-43-7
benzyl (2S,3S)-2-<(R)-2-<(tert-butyl)dimethylsilyloxy>tridecyl>-3-hexyl-4-oxoazetidine-1-acetate

: 160452-49-3
benzyl (2S,3S)-3-hexyl-2-<(R)-2-hydroxytridecyl>-4-oxoazetidine-1-acetate

Guidance literature:: With hydrogen fluoride; In acetonitrile; at 0 ℃; for 2h;
DOI:10.1002/hlca.19940770420

Reference yield:

: 76062-97-0
methyl (R)-3-hydroxytetradecanoate

: 160452-49-3
benzyl (2S,3S)-3-hexyl-2-<(R)-2-hydroxytridecyl>-4-oxoazetidine-1-acetate

Guidance literature:: Multi-step reaction with 9 steps

1: 100 percent / 4-(dimethylamino)pyridine, Et₃N / dimethylformamide / 16 h / Ambient temperature

2: 65 percent / DIBAH / diethyl ether; toluene / 2 h / -78 °C

3: 1.) dibutylboryl trifluoromethanesulfonate, Et(i-Pr)2N / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) CH₂Cl₂, -78 deg C, 1 h, -30 deg C, 1h

4: 1.) Me₃Al / 1.) THF, toluene, 0 deg C to r.t., 2 h, 2.) THF, toluene, r.t., 3 h

5: pyridine / 3 h / 0 °C

6: 80.8 percent / K₂CO₃ / acetone / 1 h / Heating

7: 83 percent / Na, NH₃ / tetrahydrofuran / 2 h / -78 °C

8: 63.8 percent / Cs₂CO₃ / 1,2-dimethoxy-ethane / 4 h / 120 °C

9: 91.9 percent / 40percent aq. HF / acetonitrile / 2 h / 0 °C

With dmap; di-n-butylboryl trifluoromethanesulfonate; hydrogen fluoride; ammonia; trimethylaluminum; sodium; diisobutylaluminium hydride; potassium carbonate; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; 1,2-dimethoxyethane; diethyl ether; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1002/hlca.19940770420

Reference yield:

: 111-64-8
n-octanoic acid chloride

: 160452-49-3
benzyl (2S,3S)-3-hexyl-2-<(R)-2-hydroxytridecyl>-4-oxoazetidine-1-acetate

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) BuLi / 1.) THF, -78 deg C to -20 deg C, 30 min, 2.) THF, -78 deg C to r.t.

2: 1.) dibutylboryl trifluoromethanesulfonate, Et(i-Pr)2N / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) CH₂Cl₂, -78 deg C, 1 h, -30 deg C, 1h

3: 1.) Me₃Al / 1.) THF, toluene, 0 deg C to r.t., 2 h, 2.) THF, toluene, r.t., 3 h

4: pyridine / 3 h / 0 °C

5: 80.8 percent / K₂CO₃ / acetone / 1 h / Heating

6: 83 percent / Na, NH₃ / tetrahydrofuran / 2 h / -78 °C

7: 63.8 percent / Cs₂CO₃ / 1,2-dimethoxy-ethane / 4 h / 120 °C

8: 91.9 percent / 40percent aq. HF / acetonitrile / 2 h / 0 °C

With n-butyllithium; di-n-butylboryl trifluoromethanesulfonate; hydrogen fluoride; ammonia; trimethylaluminum; sodium; potassium carbonate; caesium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; 1,2-dimethoxyethane; acetone; acetonitrile;
DOI:10.1002/hlca.19940770420