6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1-4)-methyl 1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate

Base Information

Chemical Name:6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1-4)-methyl 1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate
CAS No.:1394857-46-5
Molecular Formula:C₄₁H₄₇N₃O₁₅
Molecular Weight:821.835
Hs Code.:

Synonyms:6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1-4)-methyl 1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate

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Chemical Property of 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1-4)-methyl 1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate

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Technology Process of 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1-4)-methyl 1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate

There total 11 articles about 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1-4)-methyl 1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate 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: 67.0%

: 735326-84-8
methyl 1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate

: 134221-38-8
6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-(p-methoxybenzyl)-D-glucopyranosyl trichloroacetamidate

: 1394857-46-5
6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1-4)-methyl 1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -25 ℃; for 1h; Molecular sieve; Inert atmosphere;
DOI:10.1021/jo300722y

Reference yield: 59.0%

: phenyl 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-1-thio-α-D-glucopyranoside

: 735326-84-8
methyl 1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate

: 1394857-46-5
6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1-4)-methyl 1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate

Guidance literature:: With N-iodo-succinimide; silver trifluoromethanesulfonate; In dichloromethane; for 0.25h; Molecular sieve;
DOI:10.1021/jo300722y

Reference yield:

: 56883-33-1
2-azido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranosyl acetate

: 1394857-46-5
6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1-4)-methyl 1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate

Guidance literature:: Multi-step reaction with 7 steps

1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 144 h / 20 °C / Inert atmosphere

2: methanol; sodium / 1.5 h / Inert atmosphere

3: camphorsulfonic acid / acetonitrile / 16 h

4: sodium hydride / N,N-dimethyl-formamide; mineral oil / 5.5 h / Inert atmosphere

5: borane-THF; di-n-butylboryl trifluoromethanesulfonate / dichloromethane; tetrahydrofuran / 0 °C

6: dmap; pyridine / dichloromethane / 2 h / 0 - 20 °C

7: N-iodo-succinimide; silver trifluoromethanesulfonate / dichloromethane / 0.25 h / Molecular sieve

With pyridine; methanol; dmap; N-iodo-succinimide; borane-THF; trimethylsilyl trifluoromethanesulfonate; di-n-butylboryl trifluoromethanesulfonate; camphorsulfonic acid; silver trifluoromethanesulfonate; sodium; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; mineral oil;
DOI:10.1021/jo300722y