(2S,3S,4R)-3,4-Bis(benzoyloxy)-2-<(R)-2-(benzoyloxy)tetracosanoylamino>-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)hexadecane

Base Information

• Chemical Name: (2S,3S,4R)-3,4-Bis(benzoyloxy)-2-<(R)-2-(benzoyloxy)tetracosanoylamino>-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)hexadecane
• CAS No.: 128802-70-0
• Molecular Formula: C₇₅H₁₁₁NO₁₇
• Molecular Weight: 1298.7
• Mol file: 128802-70-0.mol

Synonyms:

Chemical Property of (2S,3S,4R)-3,4-Bis(benzoyloxy)-2-<(R)-2-(benzoyloxy)tetracosanoylamino>-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)hexadecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R)-3,4-Bis(benzoyloxy)-2-<(R)-2-(benzoyloxy)tetracosanoylamino>-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)hexadecane

There total 12 articles about (2S,3S,4R)-3,4-Bis(benzoyloxy)-2-<(R)-2-(benzoyloxy)tetracosanoylamino>-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)hexadecane 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: 72.0%

(2S,3S,4R)-2-[(R)-2-(Benzoyloxy)tetracosanoylamino]-3,4-(dibenzoyloxy)-1-hexadecanol (128802-69-7) + 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl trichloroacetimidate (92052-29-4) → (2S,3S,4R)-1-Acetoxy-3,4-bis(benzoyloxy)-2-<(R)-2-benzoyloxy)tetracosanoylamino>hexadecane (128802-71-1) + (2S,3S,4R)-3,4-Bis(benzoyloxy)-2-<(R)-2-(benzoyloxy)tetracosanoylamino>-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)hexadecane (128802-70-0)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; for 15h; Ambient temperature;

Reference yield:

1-Heneicosyne (61847-81-2) → (2S,3S,4R)-3,4-Bis(benzoyloxy)-2-<(R)-2-(benzoyloxy)tetracosanoylamino>-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)hexadecane (128802-70-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 72 percent / n-BuLi, HMPA / hexane; tetrahydrofuran / 1 h / Ambient temperature

2: 89 percent / i-Pr₂NEt / 14 h / Ambient temperature

3: 100 percent / H₂ / PtO₂*2H₂O / propan-2-ol / 2.5 h / 760 Torr

4: 89 percent / cyclohexene / 10percent Pd/C / ethanol / 4 h / Heating

5: 77 percent / pyridinium dichromate / dimethylformamide / 7 h / 50 °C

6: 66 percent / DCC, N-ethylmorpholine, HOBt / tetrahydrofuran / 35 h / Ambient temperature

7: 90 percent / B₃*Et₂O, Me₂S / CH₂Cl₂ / 1 h / Ambient temperature

9: 72 percent / BF₃*Et₂O, 4A molecular sieves / CH₂Cl₂ / 15 h / Ambient temperature

With N-ethylmorpholine;; N,N,N,N,N,N-hexamethylphosphoric triamide; dipyridinium dichromate; n-butyllithium; dimethylsulfide; 4 A molecular sieve; B₃*Et₂O; boron trifluoride diethyl etherate; hydrogen; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; cyclohexene; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;

Reference yield:

(R)-1-(Benzyloxy)-4-tetracosyn-2-ol (126960-18-7) → (2S,3S,4R)-3,4-Bis(benzoyloxy)-2-<(R)-2-(benzoyloxy)tetracosanoylamino>-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)hexadecane (128802-70-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 89 percent / i-Pr₂NEt / 14 h / Ambient temperature

2: 100 percent / H₂ / PtO₂*2H₂O / propan-2-ol / 2.5 h / 760 Torr

3: 89 percent / cyclohexene / 10percent Pd/C / ethanol / 4 h / Heating

4: 77 percent / pyridinium dichromate / dimethylformamide / 7 h / 50 °C

5: 66 percent / DCC, N-ethylmorpholine, HOBt / tetrahydrofuran / 35 h / Ambient temperature

6: 90 percent / B₃*Et₂O, Me₂S / CH₂Cl₂ / 1 h / Ambient temperature

8: 72 percent / BF₃*Et₂O, 4A molecular sieves / CH₂Cl₂ / 15 h / Ambient temperature

With N-ethylmorpholine;; dipyridinium dichromate; dimethylsulfide; 4 A molecular sieve; B₃*Et₂O; boron trifluoride diethyl etherate; hydrogen; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; cyclohexene; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;

upstream raw materials:

(2S,3S,4R)-2-[(R)-2-(Benzoyloxy)tetracosanoylamino]-3,4-(dibenzoyloxy)-1-hexadecanol

2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl trichloroacetimidate

1-Heneicosyne

(2S,3S,4R)-2-Amino-4-methoxymethoxy-hexadecane-1,3-diol