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

Base Information

• Chemical Name: (E)-(3S,4R)-1,3,4-Tris-benzyloxy-13-(2-hexyl-[1,3]dioxolan-2-yl)-tridec-6-en-2-one
• CAS No.: 78009-96-8
• Molecular Formula: C₄₃H₅₈O₆
• Molecular Weight: 670.93
• Mol file: 78009-96-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about (E)-(3S,4R)-1,3,4-Tris-benzyloxy-13-(2-hexyl-[1,3]dioxolan-2-yl)-tridec-6-en-2-one 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: 74.0%

(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) → (E)-(3S,4R)-1,3,4-Tris-benzyloxy-13-(2-hexyl-[1,3]dioxolan-2-yl)-tridec-6-en-2-one (78009-96-8)

Guidance literature:

With acetic anhydride; dimethyl sulfoxide; for 18h; Ambient temperature;

DOI:10.1139/v81-044

Reference yield:

2,3,5-Tri-O-benzyl-D-arabinose-diethylmercaptal (13036-07-2) → (E)-(3S,4R)-1,3,4-Tris-benzyloxy-13-(2-hexyl-[1,3]dioxolan-2-yl)-tridec-6-en-2-one (78009-96-8)

Guidance literature:

Multi-step reaction with 10 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

10: 74 percent / dimethylsulfoxide, acetic anhydride / 18 h / Ambient temperature

With 1H-imidazole; n-butyllithium; Celite; tetrabutyl ammonium fluoride; sodium ethanolate; sodium acetate; acetic anhydride; sodium hydride; ozone; dimethyl sulfoxide; 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)-(3S,4R)-1,3,4-Tris-benzyloxy-13-(2-hexyl-[1,3]dioxolan-2-yl)-tridec-6-en-2-one (78009-96-8)

Guidance literature:

Multi-step reaction with 8 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

8: 74 percent / dimethylsulfoxide, acetic anhydride / 18 h / Ambient temperature

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

DOI:10.1139/v81-044

upstream raw materials:

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

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