(2S,3R,4E,8E)-2-<(2R)-2-<(2R)-2-Acetoxy-2-phenylacetoxy>hexadecanoylamino>-1-(β-D-glucopyranosyloxy)-4,8-octadecadien-3-ol

Base Information

• Chemical Name: (2S,3R,4E,8E)-2-<(2R)-2-<(2R)-2-Acetoxy-2-phenylacetoxy>hexadecanoylamino>-1-(β-D-glucopyranosyloxy)-4,8-octadecadien-3-ol
• CAS No.: 114200-61-2
• Molecular Formula: C₅₀H₈₃NO₁₂
• Molecular Weight: 890.209
• Mol file: 114200-61-2.mol

Synonyms:(2S,3R,4E,8E)-2-<(2R)-2-<(2R)-2-Acetoxy-2-phenylacetoxy>hexadecanoylamino>-1-(β-D-glucopyranosyloxy)-4,8-octadecadien-3-ol

Chemical Property of (2S,3R,4E,8E)-2-<(2R)-2-<(2R)-2-Acetoxy-2-phenylacetoxy>hexadecanoylamino>-1-(β-D-glucopyranosyloxy)-4,8-octadecadien-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4E,8E)-2-<(2R)-2-<(2R)-2-Acetoxy-2-phenylacetoxy>hexadecanoylamino>-1-(β-D-glucopyranosyloxy)-4,8-octadecadien-3-ol

There total 14 articles about (2S,3R,4E,8E)-2-<(2R)-2-<(2R)-2-Acetoxy-2-phenylacetoxy>hexadecanoylamino>-1-(β-D-glucopyranosyloxy)-4,8-octadecadien-3-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: 87.0%

(2S,3R,4E,8E)-2-Amino-1-(β-D-glucopyranosyloxy)-4,8-octadecadien-3-ol (114200-59-8) + (R)-2-((R)-2-Acetoxy-2-phenyl-acetoxy)-hexadecanoic acid (114200-60-1) → (2S,3R,4E,8E)-2-<(2R)-2-<(2R)-2-Acetoxy-2-phenylacetoxy>hexadecanoylamino>-1-(β-D-glucopyranosyloxy)-4,8-octadecadien-3-ol (114200-61-2)

Guidance literature:

With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In ethanol; at 50 ℃; for 5h;

Reference yield:

caprinaldehyde (112-31-2) → (2S,3R,4E,8E)-2-<(2R)-2-<(2R)-2-Acetoxy-2-phenylacetoxy>hexadecanoylamino>-1-(β-D-glucopyranosyloxy)-4,8-octadecadien-3-ol (114200-61-2)

Guidance literature:

Multi-step reaction with 15 steps

1: 84 percent / tetrahydrofuran / 0.5 h / -20 °C

2: 81 percent / propionsaeure / 3 h / Heating

3: 95 percent / LiAlH₄ / diethyl ether

4: 71 percent / pyridine, PBr₃ / hexane / Heating from -20 deg C to room temperature.

5: 100 percent / 12 h / 140 °C

6: C₆H₅Li / 1.) diethyl ether; 2.) toluene, THF, -35 deg C, 20 min.

7: 1.) pyridine, (CF₃CO)2O, 2.) NaN₃ / 1.) CH₂Cl₂, -15 deg C, 15 min; 2.) CH₂Cl₂, DMF, room temperature, 5 h

8: 53 percent / p-toluenesulfonic acid monohydrate / methanol / 12 h / Ambient temperature

9: 96 percent / tetrahydrofuran; pyridine; CHCl₃ / 24 h / Ambient temperature

10: 88 percent / toluene; pyridine / 12 h / Ambient temperature

11: 96 percent / BF₃-(C₂H₅)2O / toluene; methanol / 8 h / Ambient temperature

12: 82 percent / BF₃-Et₂O / CH₂Cl₂; hexane / 5 h

13: 96 percent / CH₃ONa / methanol / 4 h / Ambient temperature

14: 97 percent / H₂S / pyridine; H₂O / 12 h

15: 87 percent / EEDQ / ethanol / 5 h / 50 °C

With pyridine; lithium aluminium tetrahydride; sodium azide; boron trifluoride diethyl etherate; hydrogen sulfide; sodium methylate; phosphorus tribromide; toluene-4-sulfonic acid; propionic acid; phenyllithium; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; trifluoroacetic anhydride; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; hexane; dichloromethane; chloroform; water; toluene;

Reference yield:

1-dodecen-3-ol (4048-42-4) → (2S,3R,4E,8E)-2-<(2R)-2-<(2R)-2-Acetoxy-2-phenylacetoxy>hexadecanoylamino>-1-(β-D-glucopyranosyloxy)-4,8-octadecadien-3-ol (114200-61-2)

Guidance literature:

Multi-step reaction with 14 steps

1: 81 percent / propionsaeure / 3 h / Heating

2: 95 percent / LiAlH₄ / diethyl ether

3: 71 percent / pyridine, PBr₃ / hexane / Heating from -20 deg C to room temperature.

4: 100 percent / 12 h / 140 °C

5: C₆H₅Li / 1.) diethyl ether; 2.) toluene, THF, -35 deg C, 20 min.

6: 1.) pyridine, (CF₃CO)2O, 2.) NaN₃ / 1.) CH₂Cl₂, -15 deg C, 15 min; 2.) CH₂Cl₂, DMF, room temperature, 5 h

7: 53 percent / p-toluenesulfonic acid monohydrate / methanol / 12 h / Ambient temperature

8: 96 percent / tetrahydrofuran; pyridine; CHCl₃ / 24 h / Ambient temperature

9: 88 percent / toluene; pyridine / 12 h / Ambient temperature

10: 96 percent / BF₃-(C₂H₅)2O / toluene; methanol / 8 h / Ambient temperature

11: 82 percent / BF₃-Et₂O / CH₂Cl₂; hexane / 5 h

12: 96 percent / CH₃ONa / methanol / 4 h / Ambient temperature

13: 97 percent / H₂S / pyridine; H₂O / 12 h

14: 87 percent / EEDQ / ethanol / 5 h / 50 °C

With pyridine; lithium aluminium tetrahydride; sodium azide; boron trifluoride diethyl etherate; hydrogen sulfide; sodium methylate; phosphorus tribromide; toluene-4-sulfonic acid; propionic acid; phenyllithium; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; trifluoroacetic anhydride; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; hexane; dichloromethane; chloroform; water; toluene;

upstream raw materials:

(2S,3R,4E,8E)-2-Amino-1-(β-D-glucopyranosyloxy)-4,8-octadecadien-3-ol

(R)-2-((R)-2-Acetoxy-2-phenyl-acetoxy)-hexadecanoic acid

caprinaldehyde

1-dodecen-3-ol

Downstream raw materials:

(2′R)-N-{(1S,2R,3E,7E)-1-[(β-D-glucopyranosyloxy)methyl]-2-hydroxyheptadeca-3,7-dien-1-yl}-2-hydroxyhexadecanamide

Refernces