allyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)1->3(2-O-benzyl-4,6-O-benzylidene)-β-D-glucopyranoside

Base Information

• Chemical Name: allyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)1->3(2-O-benzyl-4,6-O-benzylidene)-β-D-glucopyranoside
• CAS No.: 200003-48-1
• Molecular Formula: C₃₇H₄₄O₁₅
• Molecular Weight: 728.747
• Mol file: 200003-48-1.mol

Synonyms:allyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)1->3(2-O-benzyl-4,6-O-benzylidene)-β-D-glucopyranoside

Chemical Property of allyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)1->3(2-O-benzyl-4,6-O-benzylidene)-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)1->3(2-O-benzyl-4,6-O-benzylidene)-β-D-glucopyranoside

There total 7 articles about allyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)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: 87.0%

2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate (74808-10-9,86520-63-0,87119-53-7,92052-29-4,121238-27-5,142831-80-9,127061-80-7) + allyl 2-O-benzyl-(R)-4,6-O-benzylidene-β-D-gluco-pyranoside (161277-33-4) → allyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)1->3(2-O-benzyl-4,6-O-benzylidene)-β-D-glucopyranoside (200003-48-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane;

DOI:10.1016/0040-4039(96)00177-3

Reference yield:

3,4,6-tri-O-benzoyl-D-glucal (13322-90-2) → allyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)1->3(2-O-benzyl-4,6-O-benzylidene)-β-D-glucopyranoside (200003-48-1)

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: 85 percent / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂

With trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; thionyl diimidazole; sodium methylate; 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: Schmidt glycosylation;

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

Reference yield:

3,4,6-tri-O-benzoyl-α,β-D-glucopyranose → allyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)1->3(2-O-benzyl-4,6-O-benzylidene)-β-D-glucopyranoside (200003-48-1)

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: 85 percent / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂

With trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; thionyl diimidazole; sodium methylate; 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: Schmidt glycosylation;

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

upstream raw materials:

2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate

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:

Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4S,5R,6R)-2-allyloxy-3-benzyloxy-6-benzyloxymethyl-5-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester

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

allyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)1->3(2,6-di-O-benzyl)-β-D-glucopyranoside