3′,4,4′-tri-O-benzyl-2′-O-tert-butyldimethylsilyl-3-O-[(S)-2-methyloctadecanoyl]-2-O-palmitoyl-α,α-D-trehalose

Base Information

Chemical Name:3′,4,4′-tri-O-benzyl-2′-O-tert-butyldimethylsilyl-3-O-[(S)-2-methyloctadecanoyl]-2-O-palmitoyl-α,α-D-trehalose
CAS No.:1448242-66-7
Molecular Formula:C₇₄H₁₂₀O₁₃Si
Molecular Weight:1245.84
Hs Code.:

Synonyms:3′,4,4′-tri-O-benzyl-2′-O-tert-butyldimethylsilyl-3-O-[(S)-2-methyloctadecanoyl]-2-O-palmitoyl-α,α-D-trehalose

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Chemical Property of 3′,4,4′-tri-O-benzyl-2′-O-tert-butyldimethylsilyl-3-O-[(S)-2-methyloctadecanoyl]-2-O-palmitoyl-α,α-D-trehalose

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Technology Process of 3′,4,4′-tri-O-benzyl-2′-O-tert-butyldimethylsilyl-3-O-[(S)-2-methyloctadecanoyl]-2-O-palmitoyl-α,α-D-trehalose

There total 10 articles about 3′,4,4′-tri-O-benzyl-2′-O-tert-butyldimethylsilyl-3-O-[(S)-2-methyloctadecanoyl]-2-O-palmitoyl-α,α-D-trehalose 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: 71.0%

: 1448242-62-3
3′-O-benzyl-4,6;4′,6′-di-O-benzylidene-2′-O-tert-butyldimethylsilyl-3-O-[(S)-2-methyloctadecanoyl]-2-O-palmitoyl-α,α-D-trehalose

: 1448242-66-7
3′,4,4′-tri-O-benzyl-2′-O-tert-butyldimethylsilyl-3-O-[(S)-2-methyloctadecanoyl]-2-O-palmitoyl-α,α-D-trehalose

Guidance literature:: With triethylsilane; phenylborondichloride; In dichloromethane; at -78 - -20 ℃; for 7h; regioselective reaction; Molecular sieve; Inert atmosphere;
DOI:10.1021/jo4012255

Reference yield:

: 1448242-53-2
3′-O-benzyl-4,6;4′,6′-di-O-benzylidene-2′-O-tert-butyldimethylsilyl-α,α-D-trehalose

: 1448242-66-7
3′,4,4′-tri-O-benzyl-2′-O-tert-butyldimethylsilyl-3-O-[(S)-2-methyloctadecanoyl]-2-O-palmitoyl-α,α-D-trehalose

Guidance literature:: Multi-step reaction with 3 steps

1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 5 h / 20 °C / Inert atmosphere

2: dicyclohexyl-carbodiimide; dmap / dichloromethane / 20 °C / Inert atmosphere

3: triethylsilane; phenylborondichloride / dichloromethane / 7 h / -78 - -20 °C / Molecular sieve; Inert atmosphere

With triethylsilane; dmap; phenylborondichloride; dicyclohexyl-carbodiimide; In dichloromethane;
DOI:10.1021/jo4012255

Reference yield:

: 100-52-7
benzaldehyde

: 1448242-66-7
3′,4,4′-tri-O-benzyl-2′-O-tert-butyldimethylsilyl-3-O-[(S)-2-methyloctadecanoyl]-2-O-palmitoyl-α,α-D-trehalose

Guidance literature:: Multi-step reaction with 6 steps

1: iron(III) chloride hexahydrate; triethylsilane / dichloromethane; acetonitrile / 3 h / 20 °C / Cooling with ice; Inert atmosphere

2: 2,6-dimethylpyridine / dichloromethane / 3 h / -78 °C / Inert atmosphere

3: ammonium formate; palladium 10% on activated carbon / methanol / 0.75 h / Reflux; Inert atmosphere

4: dicyclohexyl-carbodiimide; dmap / dichloromethane / 5 h / 20 °C / Inert atmosphere

5: dicyclohexyl-carbodiimide; dmap / dichloromethane / 20 °C / Inert atmosphere

6: triethylsilane; phenylborondichloride / dichloromethane / 7 h / -78 - -20 °C / Molecular sieve; Inert atmosphere

With 2,6-dimethylpyridine; triethylsilane; dmap; iron(III) chloride hexahydrate; palladium 10% on activated carbon; phenylborondichloride; ammonium formate; dicyclohexyl-carbodiimide; In methanol; dichloromethane; acetonitrile;
DOI:10.1021/jo4012255