N-oleoyl-3-O-(tert-butyldiphenylsilyl)-D-sphingosine (threo epimer)

Base Information

• Chemical Name: N-oleoyl-3-O-(tert-butyldiphenylsilyl)-D-sphingosine (threo epimer)
• CAS No.: 78779-93-8
• Molecular Formula: C₅₂H₈₇NO₃Si
• Molecular Weight: 802.353

Synonyms:N-oleoyl-3-O-(tert-butyldiphenylsilyl)-D-sphingosine (threo epimer)

Chemical Property of N-oleoyl-3-O-(tert-butyldiphenylsilyl)-D-sphingosine (threo epimer)

Chemical Property:

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Technology Process of N-oleoyl-3-O-(tert-butyldiphenylsilyl)-D-sphingosine (threo epimer)

There total 6 articles about N-oleoyl-3-O-(tert-butyldiphenylsilyl)-D-sphingosine (threo epimer) 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%

N-oleoyl-1-O-benzoyl-3-O-(tert-butyldiphenylsilyl)-D-sphingosine (threo epimer) (78779-92-7) → N-oleoyl-3-O-(tert-butyldiphenylsilyl)-D-sphingosine (threo epimer) (78779-93-8)

Guidance literature:

With methanol; sodium; at 25 ℃; for 16h;

DOI:10.1021/jo00335a015

Reference yield:

pentadec-1-yne (765-13-9) → N-oleoyl-3-O-(tert-butyldiphenylsilyl)-D-sphingosine (threo epimer) (78779-93-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) DIBAL-H / 2.) ether, toluene, warming from 5 to 23 deg C, 1 h

2: 1.27 g / 2 N HCl / tetrahydrofuran / 16 h / 25 °C

3: pyridine / 16 h / 25 °C

4: 94 percent / imidazole / dimethylformamide / 0 to 25 deg C, then 50 deg C

5: 95 percent / Na, CH₃OH / 16 h / 25 °C

With pyridine; 1H-imidazole; hydrogenchloride; methanol; sodium; diisobutylaluminium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo00335a015

Reference yield:

p-nitrophenyl oleate (17363-90-5) → N-oleoyl-3-O-(tert-butyldiphenylsilyl)-D-sphingosine (threo epimer) (78779-93-8)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 16 h / 25 °C

2: 94 percent / imidazole / dimethylformamide / 0 to 25 deg C, then 50 deg C

3: 95 percent / Na, CH₃OH / 16 h / 25 °C

With pyridine; 1H-imidazole; methanol; sodium; In N,N-dimethyl-formamide;

DOI:10.1021/jo00335a015

upstream raw materials:

N-oleoyl-1-O-benzoyl-3-O-(tert-butyldiphenylsilyl)-D-sphingosine (threo epimer)

pentadec-1-yne

p-nitrophenyl oleate

threo-4-(1-hydroxy-2-hexadecenyl)-2-phenyl-Δ²-oxazoline

Downstream raw materials:

N-oleoyl-1-O-β-D-galactosyl-3-O-(tert-butyldiphenylsilyl)-D-sphingosine (threo epimer)

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