2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α/β-D-glucopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α/β-D-glucopyranosyl trichloroacetimidate
• CAS No.: 250740-59-1
• Molecular Formula: C₂₉H₃₄Cl₃NO₁₄
• Molecular Weight: 726.946

Synonyms:2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α/β-D-glucopyranosyl trichloroacetimidate

Chemical Property of 2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α/β-D-glucopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α/β-D-glucopyranosyl trichloroacetimidate

There total 6 articles about 2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α/β-D-glucopyranosyl 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: 86.0%

trichloroacetonitrile (545-06-2) + 2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside (250740-58-0) → 2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α/β-D-glucopyranosyl trichloroacetimidate (250740-59-1)

Guidance literature:

With caesium carbonate; In dichloromethane; for 2h;

DOI:10.1002/(sici)1099-0690(199910)1999:10<2623::aid-ejoc2623>3.0.co;2-k

Reference yield:

2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate (113893-72-4) → 2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α/β-D-glucopyranosyl trichloroacetimidate (250740-59-1)

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: 81 percent / trifluoromethanesulfonic acid; N-iodosuccinimide / CH₂Cl₂; tetrahydrofuran; H₂O

5: 86 percent / cesium carbonate / CH₂Cl₂ / 2 h

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; caesium carbonate; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; 1: Etherification / 2: Acetylation / 3: Ring cleavage / 4: Substitution / 5: Esterification;

DOI:10.1002/(sici)1099-0690(199910)1999:10<2623::aid-ejoc2623>3.0.co;2-k

Reference yield:

ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside (20701-61-5,56119-28-9,131564-36-8,142924-31-0,151123-92-1,141899-53-8) → 2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α/β-D-glucopyranosyl trichloroacetimidate (250740-59-1)

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: 81 percent / trifluoromethanesulfonic acid; N-iodosuccinimide / CH₂Cl₂; tetrahydrofuran; H₂O

5: 86 percent / cesium carbonate / CH₂Cl₂ / 2 h

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; caesium carbonate; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; 1: Etherification / 2: Acetylation / 3: Ring cleavage / 4: Substitution / 5: Esterification;

DOI:10.1002/(sici)1099-0690(199910)1999:10<2623::aid-ejoc2623>3.0.co;2-k

upstream raw materials:

trichloroacetonitrile

2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside

2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate

ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside

Downstream raw materials:

2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl 4,6-O-benzylidene-3-O-(α-L-rhamnopyranosyl)-β-D-glucopyranose

2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl 2-O-phenoxyacetyl-3-O-(2,3,4-tri-O-phenoxyacetyl-α-L-rhamnopyranosyl)-β-D-glucopyranose

2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl 2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-β-D-glucopyranose

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