allyl (6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

• Chemical Name: allyl (6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS No.: 213912-97-1
• Molecular Formula: C₅₂H₅₃NO₁₇
• Molecular Weight: 963.989

Synonyms:allyl (6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property of allyl (6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl (6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 10 articles about allyl (6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-2-deoxy-2-phthalimido-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: 98.0%

allyl (6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (213912-94-8) → allyl (6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-2-deoxy-2-phthalimido-β-D-glucopyranoside (213912-97-1)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; water; for 0.5h;

DOI:10.1016/S0008-6215(98)00125-6

Reference yield:

p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (2872-65-3,14581-81-8,17042-40-9,84380-06-3,105260-62-6) → allyl (6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-2-deoxy-2-phthalimido-β-D-glucopyranoside (213912-97-1)

Guidance literature:

Multi-step reaction with 9 steps

1: NaOMe / methanol / 8 h / pH 10

2: pyridine / 4.5 h / 0 °C

3: pyridine / Ambient temperature

4: p-toluenesulfonic acid / acetonitrile; H₂O / 5 h / pH 3

5: 2-chloro-1-methylpyridinium iodide, 1,4-diazabicyclo<2.2.2>octane / 1,2-dichloro-ethane / 0.33 h

6: 88 percent / ammonium cerium(IV) nitrate / toluene; acetonitrile; H₂O / 0.5 h

7: 89 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂

8: 89 percent / 4 Angstroem molecular sieves, Me₃SiOTf / CH₂Cl₂ / 0.17 h

9: 98 percent / CF₃CO₂H / CH₂Cl₂; H₂O / 0.5 h

With 1,4-diaza-bicyclo[2.2.2]octane; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; 2-chloro-1-methyl-pyridinium iodide; sodium methylate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In pyridine; methanol; dichloromethane; water; 1,2-dichloro-ethane; toluene; acetonitrile;

DOI:10.1016/S0008-6215(98)00125-6

Reference yield:

4-methoxyphenyl 6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranoside (144367-33-9) → allyl (6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-2-deoxy-2-phthalimido-β-D-glucopyranoside (213912-97-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / ammonium cerium(IV) nitrate / toluene; acetonitrile; H₂O / 0.5 h

2: 89 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂

3: 89 percent / 4 Angstroem molecular sieves, Me₃SiOTf / CH₂Cl₂ / 0.17 h

4: 98 percent / CF₃CO₂H / CH₂Cl₂; H₂O / 0.5 h

With ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In dichloromethane; water; toluene; acetonitrile;

DOI:10.1016/S0008-6215(98)00125-6

upstream raw materials:

allyl (6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

4-methoxyphenyl 6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranoside

6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-α-D-glucopyranosyl trichloroacetimidate

Downstream raw materials:

allyl (6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranoside

(2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-Acetoxy-2-acetoxymethyl-6-allyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yloxy]-3,4,5-tris-(4-methyl-benzoyloxy)-tetrahydro-pyran-2-carboxylic acid

allyl (2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranoside

(6-O-Levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-4-O-acetyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-2-phthalimido-β-D-galactopyranosyl trichloroacetimidate

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