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

Base Information

• Chemical Name: (E)-(3R,4R)-2-Amino-3,4-bis-benzyloxy-2-benzyloxymethyl-13-(2-hexyl-[1,3]dioxolan-2-yl)-tridec-6-enenitrile
• CAS No.: 78009-97-9
• Molecular Formula: C₄₄H₆₀N₂O₅
• Molecular Weight: 696.971
• Mol file: 78009-97-9.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about (E)-(3R,4R)-2-Amino-3,4-bis-benzyloxy-2-benzyloxymethyl-13-(2-hexyl-[1,3]dioxolan-2-yl)-tridec-6-enenitrile 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: 69.0%

(E)-(3S,4R)-1,3,4-Tris-benzyloxy-13-(2-hexyl-[1,3]dioxolan-2-yl)-tridec-6-en-2-one (78009-96-8) → (E)-(3R,4R)-2-Amino-3,4-bis-benzyloxy-2-benzyloxymethyl-13-(2-hexyl-[1,3]dioxolan-2-yl)-tridec-6-enenitrile (78009-97-9,78086-20-1)

Guidance literature:

With sodium cyanide; ammonium chloride; ammonia; In methanol; at 20 - 25 ℃; for 96h;

DOI:10.1139/v81-044

Reference yield:

2,3,5-Tri-O-benzyl-D-arabinose-diethylmercaptal (13036-07-2) → (E)-(3R,4R)-2-Amino-3,4-bis-benzyloxy-2-benzyloxymethyl-13-(2-hexyl-[1,3]dioxolan-2-yl)-tridec-6-enenitrile (78009-97-9,78086-20-1)

Guidance literature:

Multi-step reaction with 11 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

11: 69 percent / ammonia, sodium cyanide, ammonium chloride / methanol / 96 h / 20 - 25 °C

With 1H-imidazole; sodium cyanide; n-butyllithium; Celite; ammonium chloride; tetrabutyl ammonium fluoride; ammonia; 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; methanol; 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)-(3R,4R)-2-Amino-3,4-bis-benzyloxy-2-benzyloxymethyl-13-(2-hexyl-[1,3]dioxolan-2-yl)-tridec-6-enenitrile (78009-97-9,78086-20-1)

Guidance literature:

Multi-step reaction with 9 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

9: 69 percent / ammonia, sodium cyanide, ammonium chloride / methanol / 96 h / 20 - 25 °C

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

DOI:10.1139/v81-044

upstream raw materials:

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

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