allyl (4,6-di-O-acetyl-3-O-allyloxycarbonyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside

Base Information

Chemical Name:allyl (4,6-di-O-acetyl-3-O-allyloxycarbonyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside
CAS No.:286476-64-0
Molecular Formula:C₄₅H₄₅NO₁₇
Molecular Weight:871.849
Hs Code.:

Synonyms:allyl (4,6-di-O-acetyl-3-O-allyloxycarbonyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside

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Chemical Property of allyl (4,6-di-O-acetyl-3-O-allyloxycarbonyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside

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Technology Process of allyl (4,6-di-O-acetyl-3-O-allyloxycarbonyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside

There total 8 articles about allyl (4,6-di-O-acetyl-3-O-allyloxycarbonyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside 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: 53.0%

: 1359944-92-5
C₂₄H₂₃Cl₃N₂O₁₁

: 286476-62-8
allyl 2,4-di-O-benzoyl-α-L-fucopyranoside

: 286476-64-0
allyl (4,6-di-O-acetyl-3-O-allyloxycarbonyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside

Guidance literature:: C₂₄H₂₃Cl₃N₂O₁₁; allyl 2,4-di-O-benzoyl-α-L-fucopyranoside; In dichloromethane; toluene; for 1.5h; Inert atmosphere; Molecular sieve;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; toluene; at 20 ℃; for 2h; Inert atmosphere;
DOI:10.1021/ja210304j

Reference yield:

: 144367-27-1
3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate

: 286476-64-0
allyl (4,6-di-O-acetyl-3-O-allyloxycarbonyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 84 percent / trimethylsilyl trifluoromethanesulfonate; 4 Angstroem sieves / CH₂Cl₂ / 0.17 h

2: aq. CF₃CO₂H / CH₂Cl₂ / 0.5 h

3: pyridine / toluene; ethanol; CH₂Cl₂

With pyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; trifluoroacetic acid; In ethanol; dichloromethane; toluene; 1: Condensation / 2: Deprotection / 3: Acetylation;
DOI:10.1016/S0957-4166(99)00585-6

Reference yield:

: 286476-61-7
allyl 2-O-benzoyl-α-L-fucopyranoside

: 286476-64-0
allyl (4,6-di-O-acetyl-3-O-allyloxycarbonyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: p-TsOH / CH₂Cl₂ / pH 3

2: AcOH / H₂O / 0.25 h / 40 °C

3: 84 percent / trimethylsilyl trifluoromethanesulfonate; 4 Angstroem sieves / CH₂Cl₂ / 0.17 h

4: aq. CF₃CO₂H / CH₂Cl₂ / 0.5 h

5: pyridine / toluene; ethanol; CH₂Cl₂

With pyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; toluene-4-sulfonic acid; acetic acid; trifluoroacetic acid; In ethanol; dichloromethane; water; toluene; 1: Acetalization / 2: Ring cleavage / 3: Condensation / 4: Deprotection / 5: Acetylation;
DOI:10.1016/S0957-4166(99)00585-6