benzyl O-β-D-glucopyranosyl-(1-3)-O-<β-D-glucopyranosyl-(1-6)>-O-(2,4-di-O-benzyl-β-D-glucopyranosyl)-(1-3)-2,4,6-tri-O-benzyl-β-D-glucopyranoside

Base Information

• Chemical Name: benzyl O-β-D-glucopyranosyl-(1-3)-O-<β-D-glucopyranosyl-(1-6)>-O-(2,4-di-O-benzyl-β-D-glucopyranosyl)-(1-3)-2,4,6-tri-O-benzyl-β-D-glucopyranoside
• CAS No.: 103078-26-8
• Molecular Formula: C₆₆H₇₈O₂₁
• Molecular Weight: 1207.33
• Mol file: 103078-26-8.mol

Synonyms:

Chemical Property of benzyl O-β-D-glucopyranosyl-(1-3)-O-<β-D-glucopyranosyl-(1-6)>-O-(2,4-di-O-benzyl-β-D-glucopyranosyl)-(1-3)-2,4,6-tri-O-benzyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl O-β-D-glucopyranosyl-(1-3)-O-<β-D-glucopyranosyl-(1-6)>-O-(2,4-di-O-benzyl-β-D-glucopyranosyl)-(1-3)-2,4,6-tri-O-benzyl-β-D-glucopyranoside

There total 12 articles about benzyl O-β-D-glucopyranosyl-(1-3)-O-<β-D-glucopyranosyl-(1-6)>-O-(2,4-di-O-benzyl-β-D-glucopyranosyl)-(1-3)-2,4,6-tri-O-benzyl-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:

benzyl bromide (100-39-0) → benzyl O-β-D-glucopyranosyl-(1-3)-O-<β-D-glucopyranosyl-(1-6)>-O-(2,4-di-O-benzyl-β-D-glucopyranosyl)-(1-3)-2,4,6-tri-O-benzyl-β-D-glucopyranoside (103078-26-8)

Guidance literature:

Multi-step reaction with 12 steps

1: 1) NaH (50percent in oil) / 1) DMF, 1 h, RT, 2) DMF, 5 h, RT

2: 85 percent / LiAlH₄, AlCl₃ / diethyl ether; CH₂Cl₂ / 2 h / Heating

3: 85 percent / tris(triphenylphosphine)rhodium(I) chloride, 1,4-diazabicyclo<2.2.2>octane / ethanol; toluene / 6 h / Heating

4: 1) NaH (50percent in oil) / 1) DMF, 1 h, RT 2) DMF, 5 h, RT

5: 83 percent / tris(triphenylphosphine)rhodium(I) chloride, 1,4-diazabicyclo<2.2.2>octane / ethanol; H₂O; toluene / 5 h / Heating

6: 83 percent / silver triflate mol. sieves 4A / 1,2-dichloro-ethane / 1) -20 deg C, 2) 0 deg C, 2 h

7: 94 percent / 1M NaOMe / methanol / 1 h / Heating

8: 87 percent / p-TsOH / acetonitrile / 5 h / Ambient temperature

9: 1) NaH (50percent in oil) / 1) DMF, 1 h, RT, 2) DMF, 5 h, RT

10: 80 percent / LiAlH₄, AlCl₃ / diethyl ether; CH₂Cl₂ / 2 h / Heating

11: 76 percent / PdCl₂, NaOAc / aq. acetic acid / 8 h / Ambient temperature

12: 1) silver triflate, mol. sieves 4A 2) 1M NaOMe / 1) toluene, nitromethane, 0 deg C, 30 min 2) MeOH, 5 h, RT

With 1,4-diaza-bicyclo[2.2.2]octane; Wilkinson's catalyst; lithium aluminium tetrahydride; aluminium trichloride; 4 A molecular sieve; sodium methylate; sodium acetate; silver trifluoromethanesulfonate; sodium hydride; toluene-4-sulfonic acid; palladium dichloride; In methanol; diethyl ether; ethanol; dichloromethane; water; acetic acid; 1,2-dichloro-ethane; toluene; acetonitrile;

DOI:10.1016/S0008-6215(00)90436-1

Reference yield:

benzyl 3-O-allyl-2,4-di-O-benzyl-β-D-glucopyranoside (103078-12-2) → benzyl O-β-D-glucopyranosyl-(1-3)-O-<β-D-glucopyranosyl-(1-6)>-O-(2,4-di-O-benzyl-β-D-glucopyranosyl)-(1-3)-2,4,6-tri-O-benzyl-β-D-glucopyranoside (103078-26-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 85 percent / tris(triphenylphosphine)rhodium(I) chloride, 1,4-diazabicyclo<2.2.2>octane / ethanol; toluene / 6 h / Heating

2: 1) NaH (50percent in oil) / 1) DMF, 1 h, RT 2) DMF, 5 h, RT

3: 83 percent / tris(triphenylphosphine)rhodium(I) chloride, 1,4-diazabicyclo<2.2.2>octane / ethanol; H₂O; toluene / 5 h / Heating

4: 83 percent / silver triflate mol. sieves 4A / 1,2-dichloro-ethane / 1) -20 deg C, 2) 0 deg C, 2 h

5: 94 percent / 1M NaOMe / methanol / 1 h / Heating

6: 87 percent / p-TsOH / acetonitrile / 5 h / Ambient temperature

7: 1) NaH (50percent in oil) / 1) DMF, 1 h, RT, 2) DMF, 5 h, RT

8: 80 percent / LiAlH₄, AlCl₃ / diethyl ether; CH₂Cl₂ / 2 h / Heating

9: 76 percent / PdCl₂, NaOAc / aq. acetic acid / 8 h / Ambient temperature

10: 1) silver triflate, mol. sieves 4A 2) 1M NaOMe / 1) toluene, nitromethane, 0 deg C, 30 min 2) MeOH, 5 h, RT

With 1,4-diaza-bicyclo[2.2.2]octane; Wilkinson's catalyst; lithium aluminium tetrahydride; aluminium trichloride; 4 A molecular sieve; sodium methylate; sodium acetate; silver trifluoromethanesulfonate; sodium hydride; toluene-4-sulfonic acid; palladium dichloride; In methanol; diethyl ether; ethanol; dichloromethane; water; acetic acid; 1,2-dichloro-ethane; toluene; acetonitrile;

DOI:10.1016/S0008-6215(00)90436-1

Reference yield:

benzyl 3-O-allyl-2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside (53929-39-8,86363-43-1,103188-94-9) → benzyl O-β-D-glucopyranosyl-(1-3)-O-<β-D-glucopyranosyl-(1-6)>-O-(2,4-di-O-benzyl-β-D-glucopyranosyl)-(1-3)-2,4,6-tri-O-benzyl-β-D-glucopyranoside (103078-26-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 85 percent / LiAlH₄, AlCl₃ / diethyl ether; CH₂Cl₂ / 2 h / Heating

2: 85 percent / tris(triphenylphosphine)rhodium(I) chloride, 1,4-diazabicyclo<2.2.2>octane / ethanol; toluene / 6 h / Heating

3: 1) NaH (50percent in oil) / 1) DMF, 1 h, RT 2) DMF, 5 h, RT

4: 83 percent / tris(triphenylphosphine)rhodium(I) chloride, 1,4-diazabicyclo<2.2.2>octane / ethanol; H₂O; toluene / 5 h / Heating

5: 83 percent / silver triflate mol. sieves 4A / 1,2-dichloro-ethane / 1) -20 deg C, 2) 0 deg C, 2 h

6: 94 percent / 1M NaOMe / methanol / 1 h / Heating

7: 87 percent / p-TsOH / acetonitrile / 5 h / Ambient temperature

8: 1) NaH (50percent in oil) / 1) DMF, 1 h, RT, 2) DMF, 5 h, RT

9: 80 percent / LiAlH₄, AlCl₃ / diethyl ether; CH₂Cl₂ / 2 h / Heating

10: 76 percent / PdCl₂, NaOAc / aq. acetic acid / 8 h / Ambient temperature

11: 1) silver triflate, mol. sieves 4A 2) 1M NaOMe / 1) toluene, nitromethane, 0 deg C, 30 min 2) MeOH, 5 h, RT

With 1,4-diaza-bicyclo[2.2.2]octane; Wilkinson's catalyst; lithium aluminium tetrahydride; aluminium trichloride; 4 A molecular sieve; sodium methylate; sodium acetate; silver trifluoromethanesulfonate; sodium hydride; toluene-4-sulfonic acid; palladium dichloride; In methanol; diethyl ether; ethanol; dichloromethane; water; acetic acid; 1,2-dichloro-ethane; toluene; acetonitrile;

DOI:10.1016/S0008-6215(00)90436-1

upstream raw materials:

2,3,4,6-tetra-O-benzoylglucosyl bromide

benzyl 2,4,6-tri-O-benzyl-3-O-(2,4-di-O-benzyl-β-D-glucopyranosyl)-β-D-glucopyranoside

benzyl bromide

benzyl 3-O-allyl-2,4-di-O-benzyl-β-D-glucopyranoside

Downstream raw materials:

benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1-3)-O-<2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1-6)>-O-(2,4-di-O-benzyl-β-D-glucopyranosyl)-(1-3)-2,4,6-tri-O-benzyl-β-D-glucopyranoside