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

Base Information

• Chemical Name: [2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-(1->4)-(6-O-acetyl-2-O-benzoyl-3-O-benzyl-α-L-idopyranosyl)-(1->4)-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-α-D-glucopyranosyl]-(1->4)-1,6-anhydro-2-O-benzoyl-3-O-benzyl-β-L-idopyranose
• CAS No.: 1374561-92-8
• Molecular Formula: C₁₁₁H₁₁₄Br₂N₆O₂₁Si₂
• Molecular Weight: 2084.13

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

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

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

There total 2 articles about [2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-(1->4)-(6-O-acetyl-2-O-benzoyl-3-O-benzyl-α-L-idopyranosyl)-(1->4)-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-α-D-glucopyranosyl]-(1->4)-1,6-anhydro-2-O-benzoyl-3-O-benzyl-β-L-idopyranose 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: 98.0%

1,6-anhydro-4-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose (1314746-09-2) + 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 trichloroacetimidate (1314746-16-1) → [2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-(1->4)-(6-O-acetyl-2-O-benzoyl-3-O-benzyl-α-L-idopyranosyl)-(1->4)-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-α-D-glucopyranosyl]-(1->4)-1,6-anhydro-2-O-benzoyl-3-O-benzyl-β-L-idopyranose (1374561-92-8)

Guidance literature:

1,6-anhydro-4-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose; 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 trichloroacetimidate; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere; Molecular sieve;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -40 - 0 ℃; for 2h; Inert atmosphere; Molecular sieve;

DOI:10.1021/ja302640p

Reference yield: 80.0%

1,6-anhydro-4-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose (1314746-09-2) + C69H70BrN3O11SSi (1314746-25-2) → [2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-(1->4)-(6-O-acetyl-2-O-benzoyl-3-O-benzyl-α-L-idopyranosyl)-(1->4)-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-α-D-glucopyranosyl]-(1->4)-1,6-anhydro-2-O-benzoyl-3-O-benzyl-β-L-idopyranose (1374561-92-8)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at -60 - -40 ℃; for 4h; Molecular sieve;

DOI:10.1021/jacs.0c00005

Reference yield: 78.0%

4-methylphenylthiotrimethylsilane (38325-59-6) + [2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-(1->4)-(6-O-acetyl-2-O-benzoyl-3-O-benzyl-α-L-idopyranosyl)-(1->4)-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-α-D-glucopyranosyl]-(1->4)-1,6-anhydro-2-O-benzoyl-3-O-benzyl-β-L-idopyranose (1374561-92-8) + acetic anhydride (108-24-7) → C120H124Br2N6O22SSi2

Guidance literature:

[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-(1->4)-(6-O-acetyl-2-O-benzoyl-3-O-benzyl-α-L-idopyranosyl)-(1->4)-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-α-D-glucopyranosyl]-(1->4)-1,6-anhydro-2-O-benzoyl-3-O-benzyl-β-L-idopyranose; acetic anhydride; With copper(II) bis(trifluoromethanesulfonate); at 0 ℃; Inert atmosphere;

4-methylphenylthiotrimethylsilane; With zinc(II) iodide; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1021/jacs.0c00005

upstream raw materials:

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

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 trichloroacetimidate

C₆₉H₇₀BrN₃O₁₁SSi

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