(2S,3R,4E,8E)-1-O-(β-D-glucopyranosyl)-3-O-(t-butyldiphenylsilyl)-9-methyl-4,8-sphingadienine

Base Information

Chemical Name:(2S,3R,4E,8E)-1-O-(β-D-glucopyranosyl)-3-O-(t-butyldiphenylsilyl)-9-methyl-4,8-sphingadienine
CAS No.:160147-97-7
Molecular Formula:C₄₁H₆₅NO₇Si
Molecular Weight:712.055
Hs Code.:

Synonyms:(2S,3R,4E,8E)-1-O-(β-D-glucopyranosyl)-3-O-(t-butyldiphenylsilyl)-9-methyl-4,8-sphingadienine

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Chemical Property of (2S,3R,4E,8E)-1-O-(β-D-glucopyranosyl)-3-O-(t-butyldiphenylsilyl)-9-methyl-4,8-sphingadienine

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Technology Process of (2S,3R,4E,8E)-1-O-(β-D-glucopyranosyl)-3-O-(t-butyldiphenylsilyl)-9-methyl-4,8-sphingadienine

There total 6 articles about (2S,3R,4E,8E)-1-O-(β-D-glucopyranosyl)-3-O-(t-butyldiphenylsilyl)-9-methyl-4,8-sphingadienine 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: 66.0%

: 160147-96-6
(2S,3R,4E,8E)-N-trifluoroacetyl-1-O-(tetra-O-acetyl-β-D-glucopyranosyl)-3-O-(t-butyldiphenylsilyl)-9-methyl-4,8-sphingadienine

: 160147-97-7
(2S,3R,4E,8E)-1-O-(β-D-glucopyranosyl)-3-O-(t-butyldiphenylsilyl)-9-methyl-4,8-sphingadienine

Guidance literature:: With potassium hydroxide; In tetrahydrofuran; methanol; for 12h;

Reference yield:

: 160226-28-8
(2S,3R,4E,8E)-9-methyl-4,8-sphingadienine

: 160147-97-7
(2S,3R,4E,8E)-1-O-(β-D-glucopyranosyl)-3-O-(t-butyldiphenylsilyl)-9-methyl-4,8-sphingadienine

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) pyridine, 2.) MeONa / 1.) CH₂Cl₂, room temperature, 20 h, 2.) MeOH, room temperature, 1 h

2: 32 percent / pyridine / CH₂Cl₂ / 15 h / Heating

3: imidazole / dimethylformamide / 8 h / Ambient temperature

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

5: 59 percent / Hg(CN)2 / nitromethane; benzene / 3.5 h / 80 °C

6: 66 percent / aq. KOH / tetrahydrofuran; methanol / 12 h

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

Reference yield:

: 160147-93-3
(2S,3R,4E,8E)-N-trifluoroacetyl-9-methyl-4,8-sphingadienine

: 160147-97-7
(2S,3R,4E,8E)-1-O-(β-D-glucopyranosyl)-3-O-(t-butyldiphenylsilyl)-9-methyl-4,8-sphingadienine

Guidance literature:: Multi-step reaction with 5 steps

1: 32 percent / pyridine / CH₂Cl₂ / 15 h / Heating

2: imidazole / dimethylformamide / 8 h / Ambient temperature

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

4: 59 percent / Hg(CN)2 / nitromethane; benzene / 3.5 h / 80 °C

5: 66 percent / aq. KOH / tetrahydrofuran; methanol / 12 h

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