allyl (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-galactopyranoside

Base Information

• Chemical Name: allyl (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-galactopyranoside
• CAS No.: 171284-96-1
• Molecular Formula: C₆₀H₆₉NO₁₈Si
• Molecular Weight: 1120.29
• Mol file: 171284-96-1.mol

Synonyms:allyl (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-galactopyranoside

Chemical Property of allyl (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-galactopyranoside

Chemical Property:

Purity/Quality:

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)-4-O-acetyl-6-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-β-D-galactopyranoside

There total 13 articles about allyl (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-galactopyranoside 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:

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)-4-O-acetyl-6-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-β-D-galactopyranoside (171284-96-1)

Guidance literature:

Multi-step reaction with 12 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

10: 96 percent / pyridine / 6 h / 0 °C

11: CH₂Cl₂; pyridine / 6 h / 0 °C

12: dimethylformamide / Ambient temperature

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; N,N-dimethyl-formamide; 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)-4-O-acetyl-6-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-β-D-galactopyranoside (171284-96-1)

Guidance literature:

Multi-step reaction with 7 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

5: 96 percent / pyridine / 6 h / 0 °C

6: CH₂Cl₂; pyridine / 6 h / 0 °C

7: dimethylformamide / Ambient temperature

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

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

Reference yield:

6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-α-D-glucopyranosyl trichloroacetimidate (144367-26-0) → allyl (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-galactopyranoside (171284-96-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 89 percent / 4 Angstroem molecular sieves, Me₃SiOTf / CH₂Cl₂ / 0.17 h

2: 98 percent / CF₃CO₂H / CH₂Cl₂; H₂O / 0.5 h

3: 96 percent / pyridine / 6 h / 0 °C

4: CH₂Cl₂; pyridine / 6 h / 0 °C

5: dimethylformamide / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; trifluoroacetic acid; In pyridine; dichloromethane; water; N,N-dimethyl-formamide;

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

upstream raw materials:

tetrabutylammonium acetate

allyl (6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-6-O-tert-butyldimethylsilyl-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

Downstream raw materials:

(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

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

(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 (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

Refernces

• 1、 Halkes, Koen M.,Slaghek, Ted M.,Vermeer, Henricus J.,Kamerling, Johannis P.,Vliegenthart, Johannes F. G.. "Synthesis of a Tetrasaccharide Fragment of the Circulating Anodic Antigen of Schistosoma mansoni". . p. 6137 - 6140. Retrieved 2007/10/02.