(2S,3R,4E,8E,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,8E,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.:262592-98-3
Molecular Formula:C₇₂H₉₅NO₁₅
Molecular Weight:1214.54
Hs Code.:

Synonyms:(2S,3R,4E,8E,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

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Chemical Property of (2S,3R,4E,8E,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

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Technology Process of (2S,3R,4E,8E,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 7 articles about (2S,3R,4E,8E,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: 78.0%

: 14218-11-2
2,3,4,6-tetra-O-benzoylglucosyl bromide

: 262592-97-2
(2S,3R,4E,8E,2'R)-3-acetoxy-2-(2'-acetoxyhexadecanoyl)amino-4,8-octadien-1-ol

: 262592-98-3
(2S,3R,4E,8E,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

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:

: 115031-71-5
(2S,3R,2'R,4E,8E)-2-(hexadecanoylamino)-4,8-octadecadiene-1,3,2′-triol

: 262592-98-3
(2S,3R,4E,8E,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

Guidance literature:: Multi-step reaction with 4 steps

1: 82 percent / imidazole / CH₂Cl₂; dimethylformamide / 0.5 h / 0 °C

2: 90 mg / DMAP; pyridine / CH₂Cl₂ / 2 h / 5 - 10 °C

3: 53 mg / AcOH; TBAF / tetrahydrofuran / 3 h / 20 °C

4: 78 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

Reference yield:

: 115018-44-5
(2S,3R,4E,8E,2'R)-2-(2'-acetoxyhexadecanoyl)amino-1-O-benzoyl-4,8-octadiene-1,3-diol

: 262592-98-3
(2S,3R,4E,8E,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

Guidance literature:: Multi-step reaction with 5 steps

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

2: 82 percent / imidazole / CH₂Cl₂; dimethylformamide / 0.5 h / 0 °C

3: 90 mg / DMAP; pyridine / CH₂Cl₂ / 2 h / 5 - 10 °C

4: 53 mg / AcOH; TBAF / tetrahydrofuran / 3 h / 20 °C

5: 78 percent / molecular sieves 4A; AgOTf / CH₂Cl₂; toluene / 2 h / -20 - 0 °C

With pyridine; 1H-imidazole; dmap; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium methylate; silver trifluoromethanesulfonate; acetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Hydrolysis / 2: Substitution / 3: Acetylation / 4: Substitution / 5: Substitution;
DOI:10.1016/S0040-4020(99)01018-2