(3S,4S,2'S)-3-hexyl-4-(2'-benzyloxytridec-1'-yl)oxetan-2-one

Base Information

• Chemical Name: (3S,4S,2'S)-3-hexyl-4-(2'-benzyloxytridec-1'-yl)oxetan-2-one
• CAS No.: 134453-14-8
• Molecular Formula: C₂₉H₄₈O₃
• Molecular Weight: 444.698
• Mol file: 134453-14-8.mol

Synonyms:(3S,4S,2'S)-3-hexyl-4-(2'-benzyloxytridec-1'-yl)oxetan-2-one

Chemical Property of (3S,4S,2'S)-3-hexyl-4-(2'-benzyloxytridec-1'-yl)oxetan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S,2'S)-3-hexyl-4-(2'-benzyloxytridec-1'-yl)oxetan-2-one

There total 30 articles about (3S,4S,2'S)-3-hexyl-4-(2'-benzyloxytridec-1'-yl)oxetan-2-one 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: 75.0%

(2S,3S,5S)-5-(benzyloxy)-2-hexyl-3-hydroxyhexadecanoic acid (134453-13-7) → (3S,4S,2'S)-3-hexyl-4-(2'-benzyloxytridec-1'-yl)oxetan-2-one (134453-14-8)

Guidance literature:

With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; In dichloromethane; at 23 ℃; for 1h;

DOI:10.1016/j.tetlet.2007.11.051

Reference yield:

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) → (3S,4S,2'S)-3-hexyl-4-(2'-benzyloxytridec-1'-yl)oxetan-2-one (134453-14-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 91 percent / TfOH / cyclohexane; CH₂Cl₂ / 0.5 h / Ambient temperature

2: 98 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature

3: 88 percent / PDC / dimethylformamide / 2 h / Ambient temperature

4: 62 percent / Jones' reagent / acetone / 0.75 h / 0 °C

5: 38 percent / Hg(OAc)2, AcOOH, AcOH / 3 h / Ambient temperature

6: benzenesulfonyl chloride, pyridine / 15 h / 0 °C

With pyridine; peracetic acid; dipyridinium dichromate; jones' reagent; trifluorormethanesulfonic acid; mercury(II) diacetate; tetrabutyl ammonium fluoride; acetic acid; benzenesulfonyl chloride; In tetrahydrofuran; dichloromethane; cyclohexane; N,N-dimethyl-formamide; acetone;

DOI:10.1039/a804275f

Reference yield:

(3S,4S,6S)-4-<(tert-butyldimethylsilyl)oxy>-3-hexyl-6-undecyltetrahydro-2H-pyran-2-one (134360-67-1) → (3S,4S,2'S)-3-hexyl-4-(2'-benzyloxytridec-1'-yl)oxetan-2-one (134453-14-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) aq. KOH / 1) dioxane, 80 min, 2) THF, hexamethylphosphorus triamide, 16 h, RT

2: 71 percent / trifluoromethansulfonic acid / CH₂Cl₂; cyclohexane / 5 h / Ambient temperature

3: 94 percent / aq. HF / acetonitrile; tetrahydrofuran / 2 h / 0 °C

4: 99 percent / aq. NaOH / ethanol / 4 h / 50 °C

5: 69 percent / pyridine, benzenesulfonyl chloride / 17 h / 0 °C

With pyridine; potassium hydroxide; sodium hydroxide; trifluorormethanesulfonic acid; hydrogen fluoride; benzenesulfonyl chloride; In tetrahydrofuran; ethanol; dichloromethane; cyclohexane; acetonitrile;

DOI:10.1021/jo00015a027

upstream raw materials:

(2S,3S,5S)-5-(benzyloxy)-2-hexyl-3-hydroxyhexadecanoic acid

tridec-1-yne

O-benzyl 2,2,2-trichloroacetimidate

(E)-1-dimethyl(phenyl)silyltridec-1-ene

Downstream raw materials:

(3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one

N-[(phenylmethoxy)carbonyl]-L-leucine (1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester

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