(3S,4R,5E)-1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-4-hydroxy-3-[15(Z)-tetracosenoylamino]-5-nonadecene

Base Information

• Chemical Name: (3S,4R,5E)-1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-4-hydroxy-3-[15(Z)-tetracosenoylamino]-5-nonadecene
• CAS No.: 906545-92-4
• Molecular Formula: C₇₇H₁₁₇NO₇
• Molecular Weight: 1168.78

Synonyms:(3S,4R,5E)-1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-4-hydroxy-3-[15(Z)-tetracosenoylamino]-5-nonadecene

Chemical Property of (3S,4R,5E)-1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-4-hydroxy-3-[15(Z)-tetracosenoylamino]-5-nonadecene

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of (3S,4R,5E)-1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-4-hydroxy-3-[15(Z)-tetracosenoylamino]-5-nonadecene

There total 14 articles about (3S,4R,5E)-1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-4-hydroxy-3-[15(Z)-tetracosenoylamino]-5-nonadecene 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:

(2,3,4,6-tetra-O-benzyl-1-C-vinyl-α-D-galactopyranosyloxy)-ethanoic acid (906545-77-5) → (3S,4R,5E)-1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-4-hydroxy-3-[15(Z)-tetracosenoylamino]-5-nonadecene (906545-92-4)

Guidance literature:

Multi-step reaction with 12 steps

1.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C

2.1: 1.60 g / diethyl ether / 0 °C

3.1: 91 percent / hydrogen / Pt/C / methanol / 5 h / 20 °C

4.1: 90 percent / triphenylphosphine; DMAP; diethyl azodicarboxylate / tetrahydrofuran / 2 h / 70 °C

5.1: 90 percent / sodium azide / dimethylformamide / 1 h / 85 °C

6.1: hydrogen sulfide; pyridine / H₂O / 18 h / 20 °C

7.1: 1.05 g / pyridine / CH₂Cl₂ / 4 h / 20 °C

8.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

8.2: 80 percent / tetrahydrofuran; hexane / -78 - 20 °C

9.1: 71 percent / potassium carbonate / tetrahydrofuran; acetonitrile / 18 h / 20 °C

10.1: L-Selectride

11.1: aq. HCl / dioxane / 4 h / 70 °C

12.1: 0.13 g / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 4 h / 20 °C

With pyridine; hydrogenchloride; dmap; n-butyllithium; sodium azide; hydrogen sulfide; hydrogen; L-Selectride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; platinum on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; n-heptane; dichloromethane; ethylbenzene; water; N,N-dimethyl-formamide; acetonitrile; 1.1: <2,3>-Wittig sigmatropic rearrangement / 4.1: Mitsunobu reaction / 9.1: Horner-Wadsworth-Emmons olefination;

DOI:10.1021/ol061100y

Reference yield:

((2S,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-vinyl-tetrahydro-pyran-2-yloxy)-acetic acid methyl ester → (3S,4R,5E)-1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-4-hydroxy-3-[15(Z)-tetracosenoylamino]-5-nonadecene (906545-92-4)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 1.97 g / NaOH / methanol / 2 h / 20 °C

2.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C

3.1: 1.60 g / diethyl ether / 0 °C

4.1: 91 percent / hydrogen / Pt/C / methanol / 5 h / 20 °C

5.1: 90 percent / triphenylphosphine; DMAP; diethyl azodicarboxylate / tetrahydrofuran / 2 h / 70 °C

6.1: 90 percent / sodium azide / dimethylformamide / 1 h / 85 °C

7.1: hydrogen sulfide; pyridine / H₂O / 18 h / 20 °C

8.1: 1.05 g / pyridine / CH₂Cl₂ / 4 h / 20 °C

9.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

9.2: 80 percent / tetrahydrofuran; hexane / -78 - 20 °C

10.1: 71 percent / potassium carbonate / tetrahydrofuran; acetonitrile / 18 h / 20 °C

11.1: L-Selectride

12.1: aq. HCl / dioxane / 4 h / 70 °C

13.1: 0.13 g / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 4 h / 20 °C

With pyridine; hydrogenchloride; dmap; sodium hydroxide; n-butyllithium; sodium azide; hydrogen sulfide; hydrogen; L-Selectride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; platinum on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; n-heptane; dichloromethane; ethylbenzene; water; N,N-dimethyl-formamide; acetonitrile; 2.1: <2,3>-Wittig sigmatropic rearrangement / 5.1: Mitsunobu reaction / 10.1: Horner-Wadsworth-Emmons olefination;

DOI:10.1021/ol061100y

Reference yield:

(S)-2-Hydroxy-4-[(3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-(2Z)-ylidene]-butyric acid methyl ester (906545-78-6) → (3S,4R,5E)-1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-4-hydroxy-3-[15(Z)-tetracosenoylamino]-5-nonadecene (906545-92-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 91 percent / hydrogen / Pt/C / methanol / 5 h / 20 °C

2.1: 90 percent / triphenylphosphine; DMAP; diethyl azodicarboxylate / tetrahydrofuran / 2 h / 70 °C

3.1: 90 percent / sodium azide / dimethylformamide / 1 h / 85 °C

4.1: hydrogen sulfide; pyridine / H₂O / 18 h / 20 °C

5.1: 1.05 g / pyridine / CH₂Cl₂ / 4 h / 20 °C

6.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

6.2: 80 percent / tetrahydrofuran; hexane / -78 - 20 °C

7.1: 71 percent / potassium carbonate / tetrahydrofuran; acetonitrile / 18 h / 20 °C

8.1: L-Selectride

9.1: aq. HCl / dioxane / 4 h / 70 °C

10.1: 0.13 g / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 4 h / 20 °C

With pyridine; hydrogenchloride; dmap; n-butyllithium; sodium azide; hydrogen sulfide; hydrogen; L-Selectride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; diethylazodicarboxylate; platinum on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 2.1: Mitsunobu reaction / 7.1: Horner-Wadsworth-Emmons olefination;

DOI:10.1021/ol061100y

upstream raw materials:

Nervonic acid

(3'S,4'R)-3'-amino-(E)-nonadec-5'-en-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside

(2,3,4,6-tetra-O-benzyl-1-C-vinyl-α-D-galactopyranosyloxy)-ethanoic acid

methyl (2S)-2-azido-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-butanoate

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