(2S,3R,4E)-N-Trichloroacetyl-1-O-(tetra-O-acetyl-β-D-glucopyranosyl)-3-O-(tert-butyldiphenylsilyl)-4-icosasphingenine

Base Information

• Chemical Name: (2S,3R,4E)-N-Trichloroacetyl-1-O-(tetra-O-acetyl-β-D-glucopyranosyl)-3-O-(tert-butyldiphenylsilyl)-4-icosasphingenine
• CAS No.: 132910-97-5
• Molecular Formula: C₅₂H₇₆Cl₃NO₁₂Si
• Molecular Weight: 1041.62
• Mol file: 132910-97-5.mol

Synonyms:(2S,3R,4E)-N-Trichloroacetyl-1-O-(tetra-O-acetyl-β-D-glucopyranosyl)-3-O-(tert-butyldiphenylsilyl)-4-icosasphingenine

Chemical Property of (2S,3R,4E)-N-Trichloroacetyl-1-O-(tetra-O-acetyl-β-D-glucopyranosyl)-3-O-(tert-butyldiphenylsilyl)-4-icosasphingenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4E)-N-Trichloroacetyl-1-O-(tetra-O-acetyl-β-D-glucopyranosyl)-3-O-(tert-butyldiphenylsilyl)-4-icosasphingenine

There total 5 articles about (2S,3R,4E)-N-Trichloroacetyl-1-O-(tetra-O-acetyl-β-D-glucopyranosyl)-3-O-(tert-butyldiphenylsilyl)-4-icosasphingenine 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: 71.0%

(2S,3R,4E)-N-Trichloroacetyl-3-O-(tert-butyldiphenylsilyl)-4-icosasphingosine (132910-87-3) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → (2S,3R,4E)-N-Trichloroacetyl-1-O-(tetra-O-acetyl-β-D-glucopyranosyl)-3-O-(tert-butyldiphenylsilyl)-4-icosasphingenine (132910-97-5)

Guidance literature:

With mercury(II) cyanide; In nitromethane; benzene; at 80 ℃; for 1.33333h;

Reference yield:

<2(S),3(R),4E>-2-amino-4-eicosene-1,3-diol (6918-49-6) → (2S,3R,4E)-N-Trichloroacetyl-1-O-(tetra-O-acetyl-β-D-glucopyranosyl)-3-O-(tert-butyldiphenylsilyl)-4-icosasphingenine (132910-97-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) pyridine 2) NaOMe / 1) CH₂Cl₂, 15 h, r.t. 2) THF, MeOH, 30 min, r.t.

2: 86 percent / pyridine / CH₂Cl₂ / 19 h / Heating

3: imidazole / dimethylformamide / 44 h / 100 °C

4: p-TsOH*H₂O / methanol / 2 h / Ambient temperature

5: 71 percent / Hg(CN)2 / nitromethane; benzene / 1.33 h / 80 °C

With pyridine; 1H-imidazole; sodium methylate; mercury(II) cyanide; toluene-4-sulfonic acid; In methanol; nitromethane; dichloromethane; N,N-dimethyl-formamide; benzene;

Reference yield:

(2S,3R,4E)-N-Trichloroacetyl-4-icosasphingenine (132910-85-1) → (2S,3R,4E)-N-Trichloroacetyl-1-O-(tetra-O-acetyl-β-D-glucopyranosyl)-3-O-(tert-butyldiphenylsilyl)-4-icosasphingenine (132910-97-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / pyridine / CH₂Cl₂ / 19 h / Heating

2: imidazole / dimethylformamide / 44 h / 100 °C

3: p-TsOH*H₂O / methanol / 2 h / Ambient temperature

4: 71 percent / Hg(CN)2 / nitromethane; benzene / 1.33 h / 80 °C

With pyridine; 1H-imidazole; mercury(II) cyanide; toluene-4-sulfonic acid; In methanol; nitromethane; dichloromethane; N,N-dimethyl-formamide; benzene;

upstream raw materials:

(2S,3R,4E)-N-Trichloroacetyl-3-O-(tert-butyldiphenylsilyl)-4-icosasphingosine

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

<2(S),3(R),4E>-2-amino-4-eicosene-1,3-diol

(2S,3R,4E)-N-Trichloroacetyl-4-icosasphingenine

Downstream raw materials:

(2S,3R,4E)-1-O-(β-D-Glucopyranosyl)-3-O-(tert-butyldiphenylsilyl)-4-icosasphingenine