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

Base Information

• Chemical Name: 2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-α,β-D-xylopyranosyl trichloroacetimidate
• CAS No.: 321125-07-9
• Molecular Formula: C₂₇H₄₄Cl₃NO₇Si₂
• Molecular Weight: 657.179
• Mol file: 321125-07-9.mol

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

Chemical Property of 2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-α,β-D-xylopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-α,β-D-xylopyranosyl trichloroacetimidate

There total 6 articles about 2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-α,β-D-xylopyranosyl 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: 82.0%

trichloroacetonitrile (545-06-2) + 2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-α,β-D-xylopyranose → 2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-α,β-D-xylopyranosyl trichloroacetimidate (321125-07-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at -5 ℃; for 5h;

DOI:10.1016/j.tet.2016.05.049

Reference yield:

benzyl 2-O-(4-methoxybenzoyl)-α-D-xylopyranoside (219906-49-7) → 2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-α,β-D-xylopyranosyl trichloroacetimidate (321125-07-9)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; dmap; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo981685c

Reference yield:

4-Methoxy-benzoic acid (2S,3R,4R,5R)-2-benzyloxy-4,5-bis-triethylsilanyloxy-tetrahydro-pyran-3-yl ester (219906-50-0) → 2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-α,β-D-xylopyranosyl trichloroacetimidate (321125-07-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / Et₃N, H₂ / Pd/C / ethyl acetate / 24 h / 50 °C / 760 Torr

2: 79 percent / DBU / CH₂Cl₂ / 3 h / Ambient temperature

With hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium on activated charcoal; In dichloromethane; ethyl acetate;

DOI:10.1021/jo981685c

upstream raw materials:

trichloroacetonitrile

D-Xylose

benzyl 2-O-(4-methoxybenzoyl)-α-D-xylopyranoside

4-Methoxy-benzoic acid (2S,3R,4R,5R)-2-benzyloxy-4,5-bis-triethylsilanyloxy-tetrahydro-pyran-3-yl ester

Downstream raw materials:

4-methoxy-benzoic acid 2-[6-(1,5-dimethyl-2-oxo-hexyl)-6-hydroxy-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-7-yloxy]-4,5-bis-triethylsilanyloxy-tetrahydro-pyran-3-yl ester