allyl 4,6-O-benzylidene-2-O-[4,6-O-benzylidene-2-O-{4,6-O-benzylidene-2,3-di-O-p-methoxybenzyl-β-D-mannopyranosyl}-3-O-p-methoxybenzyl-α-D-mannopyranosyl]-3-O-p-methoxybenzyl-α-D-mannopyranoside

Base Information

Chemical Name:allyl 4,6-O-benzylidene-2-O-[4,6-O-benzylidene-2-O-{4,6-O-benzylidene-2,3-di-O-p-methoxybenzyl-β-D-mannopyranosyl}-3-O-p-methoxybenzyl-α-D-mannopyranosyl]-3-O-p-methoxybenzyl-α-D-mannopyranoside
CAS No.:862476-84-4
Molecular Formula:C₇₄H₈₀O₂₀
Molecular Weight:1289.44
Hs Code.:

allyl 4,6-O-benzylidene-2-O-[4,6-O-benzylidene-2-O-{4,6-O-benzylidene-2,3-di-O-p-methoxybenzyl-β-D-mannopyranosyl}-3-O-p-methoxybenzyl-α-D-mannopyranosyl]-3-O-p-methoxybenzyl-α-D-mannopyranoside

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Chemical Property of allyl 4,6-O-benzylidene-2-O-[4,6-O-benzylidene-2-O-{4,6-O-benzylidene-2,3-di-O-p-methoxybenzyl-β-D-mannopyranosyl}-3-O-p-methoxybenzyl-α-D-mannopyranosyl]-3-O-p-methoxybenzyl-α-D-mannopyranoside

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Technology Process of allyl 4,6-O-benzylidene-2-O-[4,6-O-benzylidene-2-O-{4,6-O-benzylidene-2,3-di-O-p-methoxybenzyl-β-D-mannopyranosyl}-3-O-p-methoxybenzyl-α-D-mannopyranosyl]-3-O-p-methoxybenzyl-α-D-mannopyranoside

There total 5 articles about allyl 4,6-O-benzylidene-2-O-[4,6-O-benzylidene-2-O-{4,6-O-benzylidene-2,3-di-O-p-methoxybenzyl-β-D-mannopyranosyl}-3-O-p-methoxybenzyl-α-D-mannopyranosyl]-3-O-p-methoxybenzyl-α-D-mannopyranoside 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:

: 862476-73-1
allyl-3-O-(p-methoxybenzyl)-4,6-O-benzylidene-α-D-mannopyranoside

: 862476-84-4
allyl 4,6-O-benzylidene-2-O-[4,6-O-benzylidene-2-O-{4,6-O-benzylidene-2,3-di-O-p-methoxybenzyl-β-D-mannopyranosyl}-3-O-p-methoxybenzyl-α-D-mannopyranosyl]-3-O-p-methoxybenzyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: 60 percent / TMSOTf / CH₂Cl₂ / 0.5 h / -40 °C

2.1: Ph₂SO; tri-tert-butylpyrimidine; Tf₂O / CH₂Cl₂ / 0.67 h / -40 - -20 °C

2.2: 64 percent / Et₃N / CH₂Cl₂ / -25 - 20 °C

With trifluoromethylsulfonic anhydride; trimethylsilyl trifluoromethanesulfonate; 1,1'-sulfinylbisbenzene; 2,4,5-tri-tert-butylpyrimidine; In dichloromethane;
DOI:10.1021/ol051038p

Reference yield:

: 3458-28-4
D-Mannose

: 862476-84-4
allyl 4,6-O-benzylidene-2-O-[4,6-O-benzylidene-2-O-{4,6-O-benzylidene-2,3-di-O-p-methoxybenzyl-β-D-mannopyranosyl}-3-O-p-methoxybenzyl-α-D-mannopyranosyl]-3-O-p-methoxybenzyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: BF₃*OEt₂

2.1: p-TsOH / dimethylformamide

3.1: Bu₂SnO / toluene / 3 h / Heating

3.2: 98 percent / tetrabutylammonium bromide; CsF / toluene / 1 h / Heating

4.1: 60 percent / TMSOTf / CH₂Cl₂ / 0.5 h / -40 °C

5.1: Ph₂SO; tri-tert-butylpyrimidine; Tf₂O / CH₂Cl₂ / 0.67 h / -40 - -20 °C

5.2: 64 percent / Et₃N / CH₂Cl₂ / -25 - 20 °C

With trifluoromethylsulfonic anhydride; trimethylsilyl trifluoromethanesulfonate; 1,1'-sulfinylbisbenzene; 2,4,5-tri-tert-butylpyrimidine; boron trifluoride diethyl etherate; di(n-butyl)tin oxide; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol051038p

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 862476-84-4
allyl 4,6-O-benzylidene-2-O-[4,6-O-benzylidene-2-O-{4,6-O-benzylidene-2,3-di-O-p-methoxybenzyl-β-D-mannopyranosyl}-3-O-p-methoxybenzyl-α-D-mannopyranosyl]-3-O-p-methoxybenzyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: p-TsOH / dimethylformamide

2.1: Bu₂SnO / toluene / 3 h / Heating

2.2: 98 percent / tetrabutylammonium bromide; CsF / toluene / 1 h / Heating

3.1: 60 percent / TMSOTf / CH₂Cl₂ / 0.5 h / -40 °C

4.1: Ph₂SO; tri-tert-butylpyrimidine; Tf₂O / CH₂Cl₂ / 0.67 h / -40 - -20 °C

4.2: 64 percent / Et₃N / CH₂Cl₂ / -25 - 20 °C

With trifluoromethylsulfonic anhydride; trimethylsilyl trifluoromethanesulfonate; 1,1'-sulfinylbisbenzene; 2,4,5-tri-tert-butylpyrimidine; di(n-butyl)tin oxide; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol051038p