3-O-(3'-O-acetyl-2,3-O-isopropylidene-β-D-apiofuranosyl)-2,4-di-O-benzoyl-α-D-xylopyranosyl trichloroacetimidate

Base Information

Chemical Name:3-O-(3'-O-acetyl-2,3-O-isopropylidene-β-D-apiofuranosyl)-2,4-di-O-benzoyl-α-D-xylopyranosyl trichloroacetimidate
CAS No.:685104-29-4
Molecular Formula:C₃₁H₃₂Cl₃NO₁₂
Molecular Weight:716.954
Hs Code.:

Synonyms:3-O-(3'-O-acetyl-2,3-O-isopropylidene-β-D-apiofuranosyl)-2,4-di-O-benzoyl-α-D-xylopyranosyl trichloroacetimidate

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Chemical Property of 3-O-(3'-O-acetyl-2,3-O-isopropylidene-β-D-apiofuranosyl)-2,4-di-O-benzoyl-α-D-xylopyranosyl trichloroacetimidate

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Technology Process of 3-O-(3'-O-acetyl-2,3-O-isopropylidene-β-D-apiofuranosyl)-2,4-di-O-benzoyl-α-D-xylopyranosyl trichloroacetimidate

There total 7 articles about 3-O-(3'-O-acetyl-2,3-O-isopropylidene-β-D-apiofuranosyl)-2,4-di-O-benzoyl-α-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: 89.0%

: 545-06-2
trichloroacetonitrile

: C₂₉H₃₂O₁₂

: 685104-29-4
3-O-(3'-O-acetyl-2,3-O-isopropylidene-β-D-apiofuranosyl)-2,4-di-O-benzoyl-α-D-xylopyranosyl trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1002/ejoc.200300580

Reference yield:

: 70147-50-1
2,3-O-isopropylidene-D-erythro-apiofuranoside

: 685104-29-4
3-O-(3'-O-acetyl-2,3-O-isopropylidene-β-D-apiofuranosyl)-2,4-di-O-benzoyl-α-D-xylopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 6 steps

1: 82 percent / pyridine / 0 - 20 °C

2: 49 percent / NH₃; MeOH / tetrahydrofuran / 0 °C

3: 98 percent / DBU / CH₂Cl₂ / 0.33 h / 20 °C

4: 90 percent / molecular sieves 4 Angstroem; TMSOTf / CH₂Cl₂ / 0.5 h / -15 °C

5: 100 percent / hydrogen / Pd/C / ethyl acetate; aq. ethanol / 6 h / 20 °C / 760.05 Torr

6: 89 percent / DBU / CH₂Cl₂ / 1 h / 20 °C

With pyridine; methanol; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; ammonia; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate;
DOI:10.1002/ejoc.200300580

Reference yield:

: 18403-18-4
benzyl 2,4-di-O-benzoyl-α-D-xylopyranoside

: 685104-29-4
3-O-(3'-O-acetyl-2,3-O-isopropylidene-β-D-apiofuranosyl)-2,4-di-O-benzoyl-α-D-xylopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / molecular sieves 4 Angstroem; TMSOTf / CH₂Cl₂ / 0.5 h / -15 °C

2: 100 percent / hydrogen / Pd/C / ethyl acetate; aq. ethanol / 6 h / 20 °C / 760.05 Torr

3: 89 percent / DBU / CH₂Cl₂ / 1 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In ethanol; dichloromethane; ethyl acetate;
DOI:10.1002/ejoc.200300580