(2S,3R,4E,8Z,2'R)-2-(2'-acetoxyhexadecanoyl)amino-3-O-acetyl-1-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-4,8-octadiene-1,3-diol

Base Information

• Chemical Name: (2S,3R,4E,8Z,2'R)-2-(2'-acetoxyhexadecanoyl)amino-3-O-acetyl-1-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-4,8-octadiene-1,3-diol
• CAS No.: 262593-03-3
• Molecular Formula: C₇₂H₉₅NO₁₅
• Molecular Weight: 1214.54
• Mol file: 262593-03-3.mol

Synonyms:(2S,3R,4E,8Z,2'R)-2-(2'-acetoxyhexadecanoyl)amino-3-O-acetyl-1-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-4,8-octadiene-1,3-diol

Chemical Property of (2S,3R,4E,8Z,2'R)-2-(2'-acetoxyhexadecanoyl)amino-3-O-acetyl-1-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-4,8-octadiene-1,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4E,8Z,2'R)-2-(2'-acetoxyhexadecanoyl)amino-3-O-acetyl-1-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-4,8-octadiene-1,3-diol

There total 10 articles about (2S,3R,4E,8Z,2'R)-2-(2'-acetoxyhexadecanoyl)amino-3-O-acetyl-1-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-4,8-octadiene-1,3-diol 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: 77.0%

2,3,4,6-tetra-O-benzoylglucosyl bromide (14218-11-2) + (2S,3R,4E,8Z,2'R)-3-acetoxy-2-(2'-acetoxyhexadecanoyl)amino-4,8-octadien-1-ol (262593-02-2) → (2S,3R,4E,8Z,2'R)-2-(2'-acetoxyhexadecanoyl)amino-3-O-acetyl-1-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-4,8-octadiene-1,3-diol (262593-03-3)

Guidance literature:

With 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; toluene; at -20 - 0 ℃; for 2h;

DOI:10.1016/S0040-4020(99)01018-2

Reference yield:

(4S,1'S,2'R)-4-(1',2'-Epoxybut-3'-enyl)-2-phenyl-4,5-dihydrooxazole (173531-24-3) → (2S,3R,4E,8Z,2'R)-2-(2'-acetoxyhexadecanoyl)amino-3-O-acetyl-1-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-4,8-octadiene-1,3-diol (262593-03-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 92 percent / LDA; CuI / tetrahydrofuran / -70 - -10 °C

2: 91 percent / iBu₂AlH / toluene / 0.83 h / -70 - -50 °C

3: 78 percent / t-BuOK / tetrahydrofuran / -70 - 0 °C

4: 145 mg / aq. HCl / tetrahydrofuran / 16 h / 20 °C

5: 198 mg / Et₃N / dimethylformamide / 6 h / 60 °C

6: 94 percent / NaOMe / CH₂Cl₂; methanol / 1 h / 0 °C

7: 91 percent / imidazole / CH₂Cl₂; dimethylformamide / 0.5 h / 0 °C

8: 140 mg / DMAP; pyridine / CH₂Cl₂ / 2 h / 5 - 10 °C

9: 91 mg / AcOH; TBAF / tetrahydrofuran / 3 h / 20 °C

10: 77 percent / molecular sieves 4A; AgOTf / CH₂Cl₂; toluene / 2 h / -20 - 0 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; copper(l) iodide; 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium methylate; silver trifluoromethanesulfonate; diisobutylaluminium hydride; acetic acid; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Ring cleavage / 2: Reduction / 3: Wittig olefination / 4: Ring cleavage / 5: Acylation / 6: Hydrolysis / 7: Substitution / 8: Acetylation / 9: Substitution / 10: Substitution;

DOI:10.1016/S0040-4020(99)01018-2

Reference yield:

(2S,3R,4E,8Z,2'R)-2-(2'-hydroxyhexadecanoyl)amino-4,8-octadiene-1,3-diol (115113-95-6) → (2S,3R,4E,8Z,2'R)-2-(2'-acetoxyhexadecanoyl)amino-3-O-acetyl-1-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-4,8-octadiene-1,3-diol (262593-03-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / imidazole / CH₂Cl₂; dimethylformamide / 0.5 h / 0 °C

2: 140 mg / DMAP; pyridine / CH₂Cl₂ / 2 h / 5 - 10 °C

3: 91 mg / AcOH; TBAF / tetrahydrofuran / 3 h / 20 °C

4: 77 percent / molecular sieves 4A; AgOTf / CH₂Cl₂; toluene / 2 h / -20 - 0 °C

With pyridine; 1H-imidazole; dmap; 4 A molecular sieve; tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; acetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Substitution / 2: Acetylation / 3: Substitution / 4: Substitution;

DOI:10.1016/S0040-4020(99)01018-2

upstream raw materials:

2,3,4,6-tetra-O-benzoylglucosyl bromide

(2S,3R,4E,8Z,2'R)-3-acetoxy-2-(2'-acetoxyhexadecanoyl)amino-4,8-octadien-1-ol

(2S,3R,4E,8Z,2'R)-2-(2'-hydroxyhexadecanoyl)amino-4,8-octadiene-1,3-diol

(4S,1'R,2'E,6'Z)-4,5-dihydro-4-(1'-hydroxy-2',6'-hexadecadienyl)-2-phenyl-1,3-oxazole

Downstream raw materials:

soya-cerebroside II