2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl-(1→3)-2-O-acetyl-4-O-triethylsilyl-α,β-L-arabinopyranosyl trichloroacetimidate

Base Information

Chemical Name:2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl-(1→3)-2-O-acetyl-4-O-triethylsilyl-α,β-L-arabinopyranosyl trichloroacetimidate
CAS No.:321125-08-0
Molecular Formula:C₄₀H₆₈Cl₃NO₁₂Si₃
Molecular Weight:945.595
Hs Code.:

2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl-(1→3)-2-O-acetyl-4-O-triethylsilyl-α,β-L-arabinopyranosyl trichloroacetimidate

Synonyms:2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl-(1→3)-2-O-acetyl-4-O-triethylsilyl-α,β-L-arabinopyranosyl trichloroacetimidate

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Chemical Property of 2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl-(1→3)-2-O-acetyl-4-O-triethylsilyl-α,β-L-arabinopyranosyl trichloroacetimidate

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Technology Process of 2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl-(1→3)-2-O-acetyl-4-O-triethylsilyl-α,β-L-arabinopyranosyl trichloroacetimidate

There total 28 articles about 2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl-(1→3)-2-O-acetyl-4-O-triethylsilyl-α,β-L-arabinopyranosyl 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: 76.0%

: 545-06-2
trichloroacetonitrile

: 2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl-(1→3)-2-O-acetyl-4-O-triethylsilyl-α,β-L-arabinopyranoside

: 321125-08-0
2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl-(1→3)-2-O-acetyl-4-O-triethylsilyl-α,β-L-arabinopyranosyl trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃;
DOI:10.1016/j.tet.2015.05.058

Reference yield:

: 321125-07-9
2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-α,β-D-xylopyranosyl trichloroacetimidate

: 321125-08-0
2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl-(1→3)-2-O-acetyl-4-O-triethylsilyl-α,β-L-arabinopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) BF₃*OEt₂, 4A MS, 2.) 2,6-lutidine / 1.) CH₂Cl₂, -60 deg C, 30 min, 2.) CH₂Cl₂, -20 deg C, 1 h

2: 50 percent / H₂, Et₃N / Pd/C / ethyl acetate; ethanol / 72 h / 50 °C / 38000 Torr

3: 65 percent / DBU / CH₂Cl₂ / 6 h / Ambient temperature

With 2,6-dimethylpyridine; boron trifluoride diethyl etherate; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane; ethyl acetate;
DOI:10.1021/jo981685c

Reference yield:

: 219906-49-7
benzyl 2-O-(4-methoxybenzoyl)-α-D-xylopyranoside

: 321125-08-0
2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl-(1→3)-2-O-acetyl-4-O-triethylsilyl-α,β-L-arabinopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 6 steps

1: 93 percent / imidazole, DMAP / dimethylformamide / 1 h

2: 76 percent / Et₃N, H₂ / Pd/C / ethyl acetate / 24 h / 50 °C / 760 Torr

3: 79 percent / DBU / CH₂Cl₂ / 3 h / Ambient temperature

4: 1.) BF₃*OEt₂, 4A MS, 2.) 2,6-lutidine / 1.) CH₂Cl₂, -60 deg C, 30 min, 2.) CH₂Cl₂, -20 deg C, 1 h

5: 50 percent / H₂, Et₃N / Pd/C / ethyl acetate; ethanol / 72 h / 50 °C / 38000 Torr

6: 65 percent / DBU / CH₂Cl₂ / 6 h / Ambient temperature

With 1H-imidazole; 2,6-dimethylpyridine; dmap; boron trifluoride diethyl etherate; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo981685c