(2S,3R,4E,8Z,2'R)-3-O-(tert-butyldiphenylsilyl)-N-(2'-hydroxyhexadecanoyl)-1-O-(tetra-O-acetyl-β-D-glucopyranosyl)-4,8-sphingadienine

Base Information

• Chemical Name: (2S,3R,4E,8Z,2'R)-3-O-(tert-butyldiphenylsilyl)-N-(2'-hydroxyhexadecanoyl)-1-O-(tetra-O-acetyl-β-D-glucopyranosyl)-4,8-sphingadienine
• CAS No.: 115018-54-7
• Molecular Formula: C₆₄H₁₀₁NO₁₃Si
• Molecular Weight: 1120.59
• Mol file: 115018-54-7.mol

Synonyms:(2S,3R,4E,8Z,2'R)-3-O-(tert-butyldiphenylsilyl)-N-(2'-hydroxyhexadecanoyl)-1-O-(tetra-O-acetyl-β-D-glucopyranosyl)-4,8-sphingadienine

Chemical Property of (2S,3R,4E,8Z,2'R)-3-O-(tert-butyldiphenylsilyl)-N-(2'-hydroxyhexadecanoyl)-1-O-(tetra-O-acetyl-β-D-glucopyranosyl)-4,8-sphingadienine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4E,8Z,2'R)-3-O-(tert-butyldiphenylsilyl)-N-(2'-hydroxyhexadecanoyl)-1-O-(tetra-O-acetyl-β-D-glucopyranosyl)-4,8-sphingadienine

There total 15 articles about (2S,3R,4E,8Z,2'R)-3-O-(tert-butyldiphenylsilyl)-N-(2'-hydroxyhexadecanoyl)-1-O-(tetra-O-acetyl-β-D-glucopyranosyl)-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: 67.0%

(2S,3R,4E,8Z,2'R)-3-O-(tert-butyldiphenylsilyl)-N-(2'-hydroxyhexadecanoyl)-4,8-sphingadienine (115074-91-4) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → (2S,3R,4E,8Z,2'R)-3-O-(tert-butyldiphenylsilyl)-N-(2'-hydroxyhexadecanoyl)-1-O-(tetra-O-acetyl-β-D-glucopyranosyl)-4,8-sphingadienine (115018-54-7)

Guidance literature:

With mercury(II) cyanide; In nitromethane; benzene; at 80 ℃; for 6h;

Reference yield:

1-Bromononane (693-58-3) → (2S,3R,4E,8Z,2'R)-3-O-(tert-butyldiphenylsilyl)-N-(2'-hydroxyhexadecanoyl)-1-O-(tetra-O-acetyl-β-D-glucopyranosyl)-4,8-sphingadienine (115018-54-7)

Guidance literature:

Multi-step reaction with 14 steps

1: 1.) n-BuLi / 1.) n-hexane, THF, 1 h, -10 deg C, 2.) n-hexane, THF, HMPT, 11 h, room temperature

2: p-toluenesulfonic acid monohydrate / methanol / 18 h / Ambient temperature

3: 83 percent / H₂, quinoline / 5percent Pd/BaSO₄ / methanol / 760 Torr / Ambient temperature

4: pyridine / 9 h / 0 °C

5: dimethylsulfoxide / 18 h / Ambient temperature

6: 1.) (i-Bu)2AlH, 2.) tartaric acid / 1.) n-hexane, ether, 1 h, -20 deg C; 1 h, RT, 2.) n-hexane, ether, water, 1 h

7: 1.) triphenylphosphine / 1.) CH₂Cl₂, 0 deg C, 2.) CH₂Cl₂, 15 min, 0 deg C

8: 70 percent / n-BuLi / hexane; tetrahydrofuran / 1.) 30 min, -70 deg C, 2.) 1 h, room temperature

9: 1.) (i-Bu)2AlH / 1.) n-hexane, 3 h, 50 deg C, 2.) n-hexane, ether, toluene, 1,5 h, room temperature

10: 2 N HCl / H₂O; tetrahydrofuran / 21 h / Ambient temperature

11: pyridine / 19 h / 50 °C

12: 96 percent / imidazole / dimethylformamide / 5 h / 70 °C

13: 84 percent / NaOH / methanol; CHCl₃ / 1 h / Ambient temperature

14: 67 percent / Hg(CN)2 / benzene; nitromethane / 6 h / 80 °C

With 1H-imidazole; quinoline; hydrogenchloride; sodium hydroxide; n-butyllithium; hydrogen; mercury(II) cyanide; diisobutylaluminium hydride; toluene-4-sulfonic acid; tartaric acid; triphenylphosphine; Pd-BaSO₄; In tetrahydrofuran; pyridine; methanol; nitromethane; hexane; chloroform; water; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

Reference yield:

tridec-3-yn-1-ol (54373-82-9) → (2S,3R,4E,8Z,2'R)-3-O-(tert-butyldiphenylsilyl)-N-(2'-hydroxyhexadecanoyl)-1-O-(tetra-O-acetyl-β-D-glucopyranosyl)-4,8-sphingadienine (115018-54-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 83 percent / H₂, quinoline / 5percent Pd/BaSO₄ / methanol / 760 Torr / Ambient temperature

2: pyridine / 9 h / 0 °C

3: dimethylsulfoxide / 18 h / Ambient temperature

4: 1.) (i-Bu)2AlH, 2.) tartaric acid / 1.) n-hexane, ether, 1 h, -20 deg C; 1 h, RT, 2.) n-hexane, ether, water, 1 h

5: 1.) triphenylphosphine / 1.) CH₂Cl₂, 0 deg C, 2.) CH₂Cl₂, 15 min, 0 deg C

6: 70 percent / n-BuLi / hexane; tetrahydrofuran / 1.) 30 min, -70 deg C, 2.) 1 h, room temperature

7: 1.) (i-Bu)2AlH / 1.) n-hexane, 3 h, 50 deg C, 2.) n-hexane, ether, toluene, 1,5 h, room temperature

8: 2 N HCl / H₂O; tetrahydrofuran / 21 h / Ambient temperature

9: pyridine / 19 h / 50 °C

10: 96 percent / imidazole / dimethylformamide / 5 h / 70 °C

11: 84 percent / NaOH / methanol; CHCl₃ / 1 h / Ambient temperature

12: 67 percent / Hg(CN)2 / benzene; nitromethane / 6 h / 80 °C

With 1H-imidazole; quinoline; hydrogenchloride; sodium hydroxide; n-butyllithium; hydrogen; mercury(II) cyanide; diisobutylaluminium hydride; tartaric acid; triphenylphosphine; Pd-BaSO₄; In tetrahydrofuran; pyridine; methanol; nitromethane; hexane; chloroform; water; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

upstream raw materials:

(2S,3R,4E,8Z,2'R)-3-O-(tert-butyldiphenylsilyl)-N-(2'-hydroxyhexadecanoyl)-4,8-sphingadienine

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

1-Bromononane

tridec-3-yn-1-ol

Downstream raw materials:

soya-cerebroside II