2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-β-L-arabinopyranosyl trichloroacetimidate

Base Information

Chemical Name:2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-β-L-arabinopyranosyl trichloroacetimidate
CAS No.:852448-34-1
Molecular Formula:C₅₅H₅₀Cl₃NO₁₃
Molecular Weight:1039.36
Hs Code.:

Synonyms:2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-β-L-arabinopyranosyl trichloroacetimidate

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Chemical Property of 2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-β-L-arabinopyranosyl trichloroacetimidate

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Technology Process of 2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-β-L-arabinopyranosyl trichloroacetimidate

There total 7 articles about 2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-β-L-arabinopyranosyl trichloroacetimidate 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: 74.0%

: 852448-27-2
4-methoxybenzyl 2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-arabinopyranoside

: 545-06-2
trichloroacetonitrile

: 852448-34-1
2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-β-L-arabinopyranosyl trichloroacetimidate

Guidance literature:: 4-methoxybenzyl 2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-arabinopyranoside; With trifluoroacetic acid; In dichloromethane; water; at 20 ℃;

trichloroacetonitrile; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;
DOI:10.1016/j.tet.2005.03.003

Reference yield:

: 852448-25-0
3,4,6-tri-O-benzyl-1,2-O-[1-(ethylsulfanyl)ethylidene]-α-D-glucopyranose

: 852448-34-1
2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-β-L-arabinopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 4 steps

1.1: molecular sieves 4 Angstroem; TMSOTf / CH₂Cl₂ / 4 h / 0 °C

2.1: KOH / methanol

2.2: 3.45 g / pyridine / 6 h / 70 °C

3.1: 52 percent / molecular sieves 4 Angstroem; N-iodosuccinimide; triflic acid / CH₂Cl₂ / 2 h / 0 °C

4.1: trifluoroacetic acid / CH₂Cl₂; H₂O / 20 °C

4.2: 74 percent / DBU / CH₂Cl₂

With potassium hydroxide; N-iodo-succinimide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; trifluoroacetic acid; In methanol; dichloromethane; water;
DOI:10.1016/j.tet.2005.03.003

Reference yield:

: 83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5
D-glucose pentaacetate

: 852448-34-1
2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-β-L-arabinopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 6 steps

1.1: HBr; acetic acid / CH₂Cl₂ / 0 - 20 °C

1.2: 83 percent / 2,6-lutidine; tetrabutylammonium bromide / nitromethane / 48 h / 20 °C

2.1: 55 percent / KOH / tetrahydrofuran / Heating

3.1: molecular sieves 4 Angstroem; TMSOTf / CH₂Cl₂ / 4 h / 0 °C

4.1: KOH / methanol

4.2: 3.45 g / pyridine / 6 h / 70 °C

5.1: 52 percent / molecular sieves 4 Angstroem; N-iodosuccinimide; triflic acid / CH₂Cl₂ / 2 h / 0 °C

6.1: trifluoroacetic acid / CH₂Cl₂; H₂O / 20 °C

6.2: 74 percent / DBU / CH₂Cl₂

With potassium hydroxide; N-iodo-succinimide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; hydrogen bromide; acetic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1016/j.tet.2005.03.003