allyl (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl-4,6-O-benzylidene)-β-D-glucopyranoside

Base Information

• Chemical Name: allyl (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl-4,6-O-benzylidene)-β-D-glucopyranoside
• CAS No.: 200003-52-7
• Molecular Formula: C₅₀H₅₄O₁₀
• Molecular Weight: 814.973

Synonyms:allyl (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl-4,6-O-benzylidene)-β-D-glucopyranoside

Chemical Property of allyl (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl-4,6-O-benzylidene)-β-D-glucopyranoside

Chemical Property:

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Technology Process of allyl (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl-4,6-O-benzylidene)-β-D-glucopyranoside

There total 7 articles about allyl (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl-4,6-O-benzylidene)-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: 76.0%

2,3,4-tri-O-benzyl-L-fucopyranosyl fluoride (127061-08-9) + allyl 2-O-benzyl-(R)-4,6-O-benzylidene-β-D-gluco-pyranoside (161277-33-4) → allyl (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl-4,6-O-benzylidene)-β-D-glucopyranoside (200003-52-7)

Guidance literature:

With 2,6-di-tert-butyl-4-methylpyridine; dibutyltin chloride; silver trifluoromethanesulfonate; In toluene; at 20 ℃; for 0.25h;

DOI:10.1016/S0040-4020(97)01024-7

Reference yield:

3,4,6-tri-O-benzoyl-D-glucal (13322-90-2) → allyl (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl-4,6-O-benzylidene)-β-D-glucopyranoside (200003-52-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 99 percent / 4-methylmorpholine N-oxide / osmium tetraoxide / acetone; H₂O; 2-methyl-propan-2-ol / 120 h

2: 88 percent / thionyl diimidazole / tetrahydrofuran / 0.33 h / -20 °C

3: 76 percent / 3 Angstroem molecular sieves / ytterbium(III) triflate / toluene / 12 h / 100 °C

4: 95 percent / trifluoromethane sulfonic acid / CH₂Cl₂; cyclohexane / 4 h / 20 °C

5: 91 percent / sodium methoxide / methanol / 12 h

6: 77 percent / p-toluenesulfonic acid / dimethylformamide / 17 h / 50 °C / reduced pressure

7: 76 percent / dibutyltin dichloride; 2,6-di-tert-butyl-4-methylpyridine; silver triflate / toluene / 0.25 h / 20 °C

With 2,6-di-tert-butyl-4-methylpyridine; trifluorormethanesulfonic acid; 3 A molecular sieve; thionyl diimidazole; dibutyltin chloride; sodium methylate; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; osmium(VIII) oxide; ytterbium(III) triflate; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 1: Oxidation / 2: Cyclization / 3: glycosylation / 4: Etherification / 5: methanolysis / 6: Cyclization / 7: glycosylation;

DOI:10.1016/S0040-4020(97)01024-7

Reference yield:

3,4,6-tri-O-benzoyl-α,β-D-glucopyranose → allyl (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl-4,6-O-benzylidene)-β-D-glucopyranoside (200003-52-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 88 percent / thionyl diimidazole / tetrahydrofuran / 0.33 h / -20 °C

2: 76 percent / 3 Angstroem molecular sieves / ytterbium(III) triflate / toluene / 12 h / 100 °C

3: 95 percent / trifluoromethane sulfonic acid / CH₂Cl₂; cyclohexane / 4 h / 20 °C

4: 91 percent / sodium methoxide / methanol / 12 h

5: 77 percent / p-toluenesulfonic acid / dimethylformamide / 17 h / 50 °C / reduced pressure

6: 76 percent / dibutyltin dichloride; 2,6-di-tert-butyl-4-methylpyridine; silver triflate / toluene / 0.25 h / 20 °C

With 2,6-di-tert-butyl-4-methylpyridine; trifluorormethanesulfonic acid; 3 A molecular sieve; thionyl diimidazole; dibutyltin chloride; sodium methylate; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; ytterbium(III) triflate; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; N,N-dimethyl-formamide; toluene; 1: Cyclization / 2: glycosylation / 3: Etherification / 4: methanolysis / 5: Cyclization / 6: glycosylation;

DOI:10.1016/S0040-4020(97)01024-7

upstream raw materials:

2,3,4-tri-O-benzyl-L-fucopyranosyl fluoride

allyl 2-O-benzyl-(R)-4,6-O-benzylidene-β-D-gluco-pyranoside

3,4,6-tri-O-benzoyl-D-glucal

allyl 3,4,6-tri-O-benzoyl-β-D-glucopyranoside

Downstream raw materials:

allyl (2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)1->4[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl-6-O-tert-butyldiphenylsilyl)]-β-D-glucopyranoside

allyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)1->4[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl-6-O-tert-butyldiphenylsilyl)]-β-D-glucopyranoside

allyl (β-D-galactopyranosyl)1->4[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl-6-O-tert-butyldiphenylsilyl)]-β-D-glucopyranoside

allyl (2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)1->4[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl)]-β-D-glucopyranoside

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