ethyl 3'-O-acetyl-2,3-O-isopropylidene-β-D-apiofuranosyl-(1->3)-2,4-di-O-benzoyl-β-D-xylopyranosyl-(1->4)-2,3-O-isopropylidene-1-thio-α-L-rhamnoside

Base Information

Chemical Name:ethyl 3'-O-acetyl-2,3-O-isopropylidene-β-D-apiofuranosyl-(1->3)-2,4-di-O-benzoyl-β-D-xylopyranosyl-(1->4)-2,3-O-isopropylidene-1-thio-α-L-rhamnoside
CAS No.:685104-30-7
Molecular Formula:C₄₀H₅₀O₁₅S
Molecular Weight:802.894
Hs Code.:

Synonyms:ethyl 3'-O-acetyl-2,3-O-isopropylidene-β-D-apiofuranosyl-(1->3)-2,4-di-O-benzoyl-β-D-xylopyranosyl-(1->4)-2,3-O-isopropylidene-1-thio-α-L-rhamnoside

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Chemical Property of ethyl 3'-O-acetyl-2,3-O-isopropylidene-β-D-apiofuranosyl-(1->3)-2,4-di-O-benzoyl-β-D-xylopyranosyl-(1->4)-2,3-O-isopropylidene-1-thio-α-L-rhamnoside

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Technology Process of ethyl 3'-O-acetyl-2,3-O-isopropylidene-β-D-apiofuranosyl-(1->3)-2,4-di-O-benzoyl-β-D-xylopyranosyl-(1->4)-2,3-O-isopropylidene-1-thio-α-L-rhamnoside

There total 8 articles about ethyl 3'-O-acetyl-2,3-O-isopropylidene-β-D-apiofuranosyl-(1->3)-2,4-di-O-benzoyl-β-D-xylopyranosyl-(1->4)-2,3-O-isopropylidene-1-thio-α-L-rhamnoside 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: 95.0%

: 127753-95-1
ethyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

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

: 685104-30-7
ethyl 3'-O-acetyl-2,3-O-isopropylidene-β-D-apiofuranosyl-(1->3)-2,4-di-O-benzoyl-β-D-xylopyranosyl-(1->4)-2,3-O-isopropylidene-1-thio-α-L-rhamnoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -50 - 20 ℃; for 0.75h;
DOI:10.1002/ejoc.200300580

Reference yield:

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

: 685104-30-7
ethyl 3'-O-acetyl-2,3-O-isopropylidene-β-D-apiofuranosyl-(1->3)-2,4-di-O-benzoyl-β-D-xylopyranosyl-(1->4)-2,3-O-isopropylidene-1-thio-α-L-rhamnoside

Guidance literature:: Multi-step reaction with 7 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

7: 95 percent / molecular sieves 4 Angstroem; TMSOTf / CH₂Cl₂ / 0.75 h / -50 - 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

: 685104-30-7
ethyl 3'-O-acetyl-2,3-O-isopropylidene-β-D-apiofuranosyl-(1->3)-2,4-di-O-benzoyl-β-D-xylopyranosyl-(1->4)-2,3-O-isopropylidene-1-thio-α-L-rhamnoside

Guidance literature:: Multi-step reaction with 4 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

4: 95 percent / molecular sieves 4 Angstroem; TMSOTf / CH₂Cl₂ / 0.75 h / -50 - 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