ethyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→3)-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:ethyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→3)-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside
CAS No.:250740-60-4
Molecular Formula:C₄₉H₄₆O₁₃S
Molecular Weight:874.962
Hs Code.:

Synonyms:ethyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→3)-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

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Chemical Property of ethyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→3)-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

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Technology Process of ethyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→3)-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

There total 8 articles about ethyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→3)-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 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: 91.0%

: 1402224-17-2
ethyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→3)-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

: 98-88-4
benzoyl chloride

: 250740-60-4
ethyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→3)-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

Guidance literature:: With pyridine; dmap; In dichloromethane; at 4 - 20 ℃; for 72h;
DOI:10.1016/j.carres.2012.07.019

Reference yield:

: 20701-61-5,56119-28-9,131564-36-8,142924-31-0,151123-92-1,141899-53-8
ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside

: 250740-60-4
ethyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→3)-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 81 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂; tetrahydrofuran / 0.5 h / -40 °C

2: 87 percent / pyridine / 12 h

3: 76 percent / trifluoromethanesulfonic acid / 1,2-dichloro-ethane / 6 h

4: NaOMe / methanol / 4 h

5: pyridine

With pyridine; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; sodium methylate; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; 1: Etherification / 2: Acetylation / 3: Ring cleavage / 4: Deacetylation / 5: Acylation;
DOI:10.1002/(sici)1099-0690(199910)1999:10<2623::aid-ejoc2623>3.0.co;2-k

Reference yield:

: 113893-72-4
2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate

: 250740-60-4
ethyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→3)-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 81 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂; tetrahydrofuran / 0.5 h / -40 °C

2: 87 percent / pyridine / 12 h

3: 76 percent / trifluoromethanesulfonic acid / 1,2-dichloro-ethane / 6 h

4: NaOMe / methanol / 4 h

5: pyridine

With pyridine; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; sodium methylate; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; 1: Etherification / 2: Acetylation / 3: Ring cleavage / 4: Deacetylation / 5: Acylation;
DOI:10.1002/(sici)1099-0690(199910)1999:10<2623::aid-ejoc2623>3.0.co;2-k