4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside trichloroacetimidate

Base Information

Chemical Name:4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside trichloroacetimidate
CAS No.:943032-63-1
Molecular Formula:C₃₆H₃₉Cl₃N₄O₉
Molecular Weight:778.086
Hs Code.:

Synonyms:4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside trichloroacetimidate

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Chemical Property of 4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside trichloroacetimidate

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Technology Process of 4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside trichloroacetimidate

There total 5 articles about 4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside 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:

: 943032-62-0
4-methoxyphenyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

: 545-06-2
trichloroacetonitrile

: 943032-63-1
4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside trichloroacetimidate

Guidance literature:: 4-methoxyphenyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside; With ammonium cerium(IV) nitrate; In water; acetonitrile; at 25 ℃; for 2h;

trichloroacetonitrile; With sodium hydride; In dichloromethane; at 25 ℃; Further stages.;
DOI:10.1002/ejoc.200601082

Reference yield:

: 870543-47-8
4-methoxyphenyl 4-O-benzyl-α-L-rhamnopyranoside

: 943032-63-1
4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside trichloroacetimidate

Guidance literature:: Multi-step reaction with 5 steps

1.1: CSA / CH₂Cl₂ / 2 h / 25 °C

1.2: 90 percent / AcOH; water / 0.5 h

2.1: 98 percent / TMSOTf / CH₂Cl₂ / 1 h / 0 °C

3.1: 83 percent / N₂H₄*AcOH / CH₂Cl₂; methanol / 12 h / 25 °C

4.1: 81 percent / NaH / dimethylformamide / 1 h / 25 °C

5.1: cerium ammonium nitrate / acetonitrile; H₂O / 2 h / 25 °C

5.2: 259 mg / NaH / CH₂Cl₂ / 25 °C

With ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; hydrazinium monoacetate; sodium hydride; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/ejoc.200601082

Reference yield:

: 943032-57-3
4-methoxyphenyl 2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

: 943032-63-1
4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside trichloroacetimidate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 98 percent / TMSOTf / CH₂Cl₂ / 1 h / 0 °C

2.1: 83 percent / N₂H₄*AcOH / CH₂Cl₂; methanol / 12 h / 25 °C

3.1: 81 percent / NaH / dimethylformamide / 1 h / 25 °C

4.1: cerium ammonium nitrate / acetonitrile; H₂O / 2 h / 25 °C

4.2: 259 mg / NaH / CH₂Cl₂ / 25 °C

With ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; hydrazinium monoacetate; sodium hydride; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/ejoc.200601082