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

Base Information

• Chemical Name: 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
• CAS No.: 1314746-09-2
• Molecular Formula: C₄₉H₅₂BrN₃O₁₀Si
• Molecular Weight: 950.955
• Mol file: 1314746-09-2.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 11 articles about 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 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: 93.0%

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) → 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)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; for 4h;

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) → 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)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 4 h

With N-iodo-succinimide; trifluorormethanesulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water;

DOI:10.1038/nchem.1073

Reference yield:

C22H41N3O4SSi3 (1314746-19-4) → 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)

Guidance literature:

Multi-step reaction with 5 steps

1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h

2: dmap; triethylamine / dichloromethane

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

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

5: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 4 h

With dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; sodium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; N,N-dimethyl-formamide;

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:

C₇₆H₈₂BrN₃O₁₈Si

C₅₈H₆₄BrN₃O₁₅Si

C₅₈H₆₂BrCl₃N₄O₁₄Si

C₅₄H₅₈BrN₃O₁₂Si