1-O-(2-O-benzoyl-3-O-levulinoyl-5-O-(triisopropylsilyl)-α-D-arabinofuranosyl) trichloroacetimidate

Base Information

Chemical Name:1-O-(2-O-benzoyl-3-O-levulinoyl-5-O-(triisopropylsilyl)-α-D-arabinofuranosyl) trichloroacetimidate
CAS No.:915149-98-3
Molecular Formula:C₂₈H₄₀Cl₃NO₈Si
Molecular Weight:653.072
Hs Code.:

Synonyms:1-O-(2-O-benzoyl-3-O-levulinoyl-5-O-(triisopropylsilyl)-α-D-arabinofuranosyl) trichloroacetimidate

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Chemical Property of 1-O-(2-O-benzoyl-3-O-levulinoyl-5-O-(triisopropylsilyl)-α-D-arabinofuranosyl) trichloroacetimidate

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Technology Process of 1-O-(2-O-benzoyl-3-O-levulinoyl-5-O-(triisopropylsilyl)-α-D-arabinofuranosyl) trichloroacetimidate

There total 11 articles about 1-O-(2-O-benzoyl-3-O-levulinoyl-5-O-(triisopropylsilyl)-α-D-arabinofuranosyl) trichloroacetimidate 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: 88.0%

: Benzoic acid (3S,4R,5R)-2-hydroxy-4-(4-oxo-pentanoyloxy)-5-triisopropylsilanyloxymethyl-tetrahydro-furan-3-yl ester

: 545-06-2
trichloroacetonitrile

: 1-O-(2-O-benzoyl-3-O-levulinoyl-5-O-(triisopropylsilyl)-β-D-arabinofuranosyl) trichloroacetimidate

: 915149-98-3
1-O-(2-O-benzoyl-3-O-levulinoyl-5-O-(triisopropylsilyl)-α-D-arabinofuranosyl) trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/jo061233x

Reference yield:

: 1,2-O-(α-allyloxybenzylidene)-β-D-arabinofuranose

: 915149-98-3
1-O-(2-O-benzoyl-3-O-levulinoyl-5-O-(triisopropylsilyl)-α-D-arabinofuranosyl) trichloroacetimidate

Guidance literature:: Multi-step reaction with 7 steps

1: 95 percent / NaH / dimethylformamide / 0 - 20 °C

2: p-toluenesulfonic acid / H₂O; 1,2-dimethoxy-ethane / 2 h / 0 - 20 °C

3: 3.71 g / DBU / CH₂Cl₂ / 0.5 h / 0 °C

4: 76 percent / imidazole / dimethylformamide / 6 h / 20 °C

5: 100 percent / 4-(dimethylamino)pyridine; N,N'-dicyclohexylcarbodiimide / CH₂Cl₂ / 1.5 h / 20 °C

6: 99 percent / p-toluenesulfonic acid / 1,2-dimethoxy-ethane / 4 h / 0 - 20 °C

7: 88 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

With 1H-imidazole; dmap; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; In 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo061233x

Reference yield:

: Benzoic acid (2S,3S,4R,5R)-4-benzyloxy-5-benzyloxymethyl-2-hydroxy-tetrahydro-furan-3-yl ester

: 915149-98-3
1-O-(2-O-benzoyl-3-O-levulinoyl-5-O-(triisopropylsilyl)-α-D-arabinofuranosyl) trichloroacetimidate

Guidance literature:: Multi-step reaction with 5 steps

1: 3.71 g / DBU / CH₂Cl₂ / 0.5 h / 0 °C

2: 76 percent / imidazole / dimethylformamide / 6 h / 20 °C

3: 100 percent / 4-(dimethylamino)pyridine; N,N'-dicyclohexylcarbodiimide / CH₂Cl₂ / 1.5 h / 20 °C

4: 99 percent / p-toluenesulfonic acid / 1,2-dimethoxy-ethane / 4 h / 0 - 20 °C

5: 88 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

With 1H-imidazole; dmap; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; In 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo061233x