6-O-acetyl-4-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-L-idopyranosyl acetate

Base Information

• Chemical Name: 6-O-acetyl-4-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-L-idopyranosyl acetate
• CAS No.: 1314746-22-9
• Molecular Formula: C₆₄H₆₆BrN₃O₁₃Si
• Molecular Weight: 1193.23

Synonyms:6-O-acetyl-4-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-L-idopyranosyl acetate

Chemical Property of 6-O-acetyl-4-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-L-idopyranosyl acetate

Chemical Property:

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Technology Process of 6-O-acetyl-4-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-L-idopyranosyl acetate

There total 6 articles about 6-O-acetyl-4-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-L-idopyranosyl acetate 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: 95.0%

1,6-anhydro-4-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose (1314746-13-8) + acetic anhydride (108-24-7) → 6-O-acetyl-4-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-L-idopyranosyl acetate (1314746-22-9)

Guidance literature:

With copper(II) bis(trifluoromethanesulfonate);

DOI:10.1038/nchem.1073

Reference yield:

p-methylphenyl 2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-1-thio-D-glucopyranoside → 6-O-acetyl-4-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-L-idopyranosyl acetate (1314746-22-9)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydride / N,N-dimethyl-formamide

2: N-iodo-succinimide; trifluorormethanesulfonic acid / dichloromethane / 4 h / -78 - -20 °C

3: copper(II) bis(trifluoromethanesulfonate)

With N-iodo-succinimide; trifluorormethanesulfonic acid; copper(II) bis(trifluoromethanesulfonate); sodium hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1038/nchem.1073

Reference yield:

p-methylphenyl 2-azido-3-O-(p-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-1-thio-D-glucopyranoside (1314746-14-9) → 6-O-acetyl-4-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-L-idopyranosyl acetate (1314746-22-9)

Guidance literature:

Multi-step reaction with 2 steps

1: N-iodo-succinimide; trifluorormethanesulfonic acid / dichloromethane / 4 h / -78 - -20 °C

2: copper(II) bis(trifluoromethanesulfonate)

With N-iodo-succinimide; trifluorormethanesulfonic acid; copper(II) bis(trifluoromethanesulfonate); In dichloromethane;

DOI:10.1038/nchem.1073

upstream raw materials:

p-methylphenyl 2-azido-3-O-(p-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-1-thio-D-glucopyranoside

C₂₂H₄₁N₃O₄SSi₃

p-methylphenyl 2-azido-2-deoxy-4-O-(2-naphthylmethyl)-1-thio-D-glucopyranoside ⁽⁴⁾

1,6-anhydro-4-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose

Downstream raw materials:

C₇₁H₇₄BrNO₁₂SSi

C₆₅H₇₂BrNO₁₄SSi

C₆₇H₇₄BrNO₁₅SSi

C₆₀H₆₆BrNO₁₂SSi

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