dl-threo-4-benzyloxy-6-hexadecyloxy-5-hydroxyhexanoic acid

Base Information

• Chemical Name: dl-threo-4-benzyloxy-6-hexadecyloxy-5-hydroxyhexanoic acid
• CAS No.: 126906-93-2
• Molecular Formula: C₂₉H₅₀O₅
• Molecular Weight: 478.713
• Mol file: 126906-93-2.mol

Synonyms:

Chemical Property of dl-threo-4-benzyloxy-6-hexadecyloxy-5-hydroxyhexanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dl-threo-4-benzyloxy-6-hexadecyloxy-5-hydroxyhexanoic acid

There total 21 articles about dl-threo-4-benzyloxy-6-hexadecyloxy-5-hydroxyhexanoic acid 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:

benzaldehyde (100-52-7) → dl-erythro-4-benzyloxy-6-hexadecyloxy-5-hydroxyhexanoic acid (126906-93-2,126907-06-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 58 percent / p-TsOH (H₂O) / toluene / 8 h / Heating

2: 65 percent / LiAlH₄-AlCl₃ / diethyl ether; CH₂Cl₂ / 3 h / Ambient temperature

3: 80 percent / p-TsOH (H₂O) / benzene / 3 h / Heating

4: 13.11 g / Et₃N / benzene / 1 h / Ambient temperature

5: 95 percent / NaI, NaHCO₃ / acetone / 14 h / Heating

6: 73 percent / 55percent NaH / dimethylformamide / 3 h / 95 °C

7: 91 percent / NaCl / dimethylsulfoxide; H₂O / 2 h / 210 °C

8: 93 percent / aq. acetic acid / 1.) room temp., 1 h, 2.) 50 deg C, 2 h

9: 83 percent / Et₃N / 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 6 h / Ambient temperature

10: 90 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 14 h / Ambient temperature

11: 98 percent / Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

12: 1.) 55percent NaH, 2.) 10percent aq. HCl / 1.) THF, room temp., 15 h; DMF, room temp., 16.5 h, 2.) DMF, 1,4-dioxane, 50 deg C, 4 h

With hydrogenchloride; lithium aluminium tetrahydride; aluminium trichloride; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; sodium iodide; sodium chloride; dmap; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; benzene;

DOI:10.1248/cpb.37.2379

Reference yield:

dl-2-O-benzyl-3,4-O-isopropylidenethreitol (84379-53-3,84379-54-4,104322-67-0,111462-38-5,116365-24-3,116405-02-8) → dl-threo-4-benzyloxy-6-hexadecyloxy-5-hydroxyhexanoic acid (126906-93-2,126907-06-0)

Guidance literature:

Multi-step reaction with 9 steps

1: Et₃N / benzene / Ambient temperature

2: NaI, NaHCO₃ / acetone / Heating

3: 55percent NaH / dimethylformamide / 95 °C

4: 87 percent / NaCl / dimethylsulfoxide; H₂O / 210 °C

5: 90 percent / aq. acetic acid / 1.) room temp., 2.) 50 deg C

6: 90 percent / Et₃N / 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / Ambient temperature

7: pyridinium p-toluenesulfonate / CH₂Cl₂ / Ambient temperature

8: Bu₄NF / tetrahydrofuran / Ambient temperature

9: 1.) 55percent NaH, 2.) 10percent aq. HCl / 1.) THF, room temp.; DMF, room temp., 2.) DMF, 1,4-dioxane, 50 deg C

With hydrogenchloride; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; triethylamine; sodium iodide; sodium chloride; dmap; pyridinium p-toluenesulfonate; In tetrahydrofuran; dichloromethane; water; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1248/cpb.37.2379

Reference yield:

dl-threo-3-O-benzyl-4-iodo-1,2-O-isopropylidenebutane-1,2,3-triol (115689-96-8,115689-98-0,127000-45-7,127000-46-8) → dl-threo-4-benzyloxy-6-hexadecyloxy-5-hydroxyhexanoic acid (126906-93-2,126907-06-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 55percent NaH / dimethylformamide / 95 °C

2: 87 percent / NaCl / dimethylsulfoxide; H₂O / 210 °C

3: 90 percent / aq. acetic acid / 1.) room temp., 2.) 50 deg C

4: 90 percent / Et₃N / 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / Ambient temperature

5: pyridinium p-toluenesulfonate / CH₂Cl₂ / Ambient temperature

6: Bu₄NF / tetrahydrofuran / Ambient temperature

7: 1.) 55percent NaH, 2.) 10percent aq. HCl / 1.) THF, room temp.; DMF, room temp., 2.) DMF, 1,4-dioxane, 50 deg C

With hydrogenchloride; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; sodium chloride; dmap; pyridinium p-toluenesulfonate; In tetrahydrofuran; dichloromethane; water; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1248/cpb.37.2379

upstream raw materials:

ethyl dl-erythro-4-benzyloxy-6-hydroxy-5-(tetrahydropyran-2-yloxy)hexanoate

hexadecanyl bromide

benzaldehyde

dl-2-O-benzyl-3,4-O-isopropylideneerythritol

Downstream raw materials:

dl-cis-4-benzyloxy-6-hexadecyloxy-5-hexanolide

dl-trans-4-benzyloxy-6-hexadecyloxy-5-hexanolide