(E)-(2R,3R,4R)-1,3,4-Tris-benzyloxy-13-(2-hexyl-[1,3]dioxolan-2-yl)-tridec-6-en-2-ol

Base Information

• Chemical Name: (E)-(2R,3R,4R)-1,3,4-Tris-benzyloxy-13-(2-hexyl-[1,3]dioxolan-2-yl)-tridec-6-en-2-ol
• CAS No.: 78009-95-7
• Molecular Formula: C₄₃H₆₀O₆
• Molecular Weight: 672.946
• Mol file: 78009-95-7.mol

Synonyms:(E)-(2R,3R,4R)-1,3,4-Tris-benzyloxy-13-(2-hexyl-[1,3]dioxolan-2-yl)-tridec-6-en-2-ol

Chemical Property of (E)-(2R,3R,4R)-1,3,4-Tris-benzyloxy-13-(2-hexyl-[1,3]dioxolan-2-yl)-tridec-6-en-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2R,3R,4R)-1,3,4-Tris-benzyloxy-13-(2-hexyl-[1,3]dioxolan-2-yl)-tridec-6-en-2-ol

There total 10 articles about (E)-(2R,3R,4R)-1,3,4-Tris-benzyloxy-13-(2-hexyl-[1,3]dioxolan-2-yl)-tridec-6-en-2-ol 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: 84.0%

[(E)-(1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-12-(2-hexyl-[1,3]dioxolan-2-yl)-dodec-5-enyloxy]-tert-butyl-dimethyl-silane (78009-92-4,78086-19-8) → (E)-(2R,3R,4R)-1,3,4-Tris-benzyloxy-13-(2-hexyl-[1,3]dioxolan-2-yl)-tridec-6-en-2-ol (78009-95-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 7h; Ambient temperature;

DOI:10.1139/v81-044

Reference yield:

2,3,5-Tri-O-benzyl-D-arabinose-diethylmercaptal (13036-07-2) → (E)-(2R,3R,4R)-1,3,4-Tris-benzyloxy-13-(2-hexyl-[1,3]dioxolan-2-yl)-tridec-6-en-2-ol (78009-95-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 95 percent / imidazole / dimethylformamide / 72 h / Ambient temperature

2: 99 percent / HgCl₂, HgO / H₂O; acetone / 1 h / Ambient temperature

4: 1.) 0.59 N EtONa, ozone; 2.) sodium hydride / 1.) ethanol; 2.) ethanol

5: 77 percent / pyridinium chlorochromate, sodium acetate, Celite / CH₂Cl₂ / 2 h / Ambient temperature

6: 86 percent / 1.) 1.6 M n-BuLi / 1.) hexane, THF; 2.) THF, hexane

7: 90 percent / m-chloroperbenzoic acid / 4.5 h / Ambient temperature

8: 1.) 0.50 M lithium diphenylphosphide; 2.) methyl iodide / 1.) THF, 30 min; 2.) 30 min, THF

9: 84 percent / 0.65 N tetra-n-butyl-ammonium fluoride / tetrahydrofuran / 7 h / Ambient temperature

With 1H-imidazole; n-butyllithium; Celite; tetrabutyl ammonium fluoride; sodium ethanolate; sodium acetate; sodium hydride; ozone; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; lithium diphenylphosphide; mercury dichloride; mercury(II) oxide; methyl iodide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1139/v81-044

Reference yield:

2,3,5-tri-O-benzyl-4-O-(tert-butyldimethylsilyl)-aldehydo-D-arabinose (78009-77-5) → (E)-(2R,3R,4R)-1,3,4-Tris-benzyloxy-13-(2-hexyl-[1,3]dioxolan-2-yl)-tridec-6-en-2-ol (78009-95-7)

Guidance literature:

Multi-step reaction with 7 steps

2: 1.) 0.59 N EtONa, ozone; 2.) sodium hydride / 1.) ethanol; 2.) ethanol

3: 77 percent / pyridinium chlorochromate, sodium acetate, Celite / CH₂Cl₂ / 2 h / Ambient temperature

4: 86 percent / 1.) 1.6 M n-BuLi / 1.) hexane, THF; 2.) THF, hexane

5: 90 percent / m-chloroperbenzoic acid / 4.5 h / Ambient temperature

6: 1.) 0.50 M lithium diphenylphosphide; 2.) methyl iodide / 1.) THF, 30 min; 2.) 30 min, THF

7: 84 percent / 0.65 N tetra-n-butyl-ammonium fluoride / tetrahydrofuran / 7 h / Ambient temperature

With n-butyllithium; Celite; tetrabutyl ammonium fluoride; sodium ethanolate; sodium acetate; sodium hydride; ozone; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; lithium diphenylphosphide; methyl iodide; In tetrahydrofuran; dichloromethane;

DOI:10.1139/v81-044

upstream raw materials:

[(E)-(1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-12-(2-hexyl-[1,3]dioxolan-2-yl)-dodec-5-enyloxy]-tert-butyl-dimethyl-silane

2,3,5-Tri-O-benzyl-D-arabinose-diethylmercaptal

2,3,5-tri-O-benzyl-4-O-(tert-butyldimethylsilyl)-aldehydo-D-arabinose

3,4,6-tri-O-benzyl-5-O-tert-butyldimethylsilyl-2-deoxy-aldehydo-D-glucose

Downstream raw materials:

(E)-(3R,4R)-2-Amino-3,4-bis-benzyloxy-2-benzyloxymethyl-13-(2-hexyl-[1,3]dioxolan-2-yl)-tridec-6-enenitrile

(E)-(3S,4R)-1,3,4-Tris-benzyloxy-13-(2-hexyl-[1,3]dioxolan-2-yl)-tridec-6-en-2-one