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

Base Information

• Chemical Name: 1,6-anhydro-4-O-[2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose
• CAS No.: 1415973-62-4
• Molecular Formula: C₆₀H₆₁N₃O₁₀Si
• Molecular Weight: 1012.24
• Mol file: 1415973-62-4.mol

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

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

There total 4 articles about 1,6-anhydro-4-O-[2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-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: 64.0%

4-methylphenyl 2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-1-thio-α/β-D-glucopyranoside (1415973-61-3) + 1,6-anhydro-2-O-benzoyl-3-O-benzyl-β-L-idopyranoside (334834-19-4) → 1,6-anhydro-4-O-[2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose (1415973-62-4) + 1,6-anhydro-4-O-[2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-β-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose (1415974-44-5)

Guidance literature:

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 - 20 ℃; for 2h; diastereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1021/ja3090065

Reference yield: 60.0%

C46H47N3O4SSi + 1,6-anhydro-2-O-benzoyl-3-O-benzyl-β-L-idopyranoside (334834-19-4) → 1,6-anhydro-4-O-[2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose (1415973-62-4)

Guidance literature:

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 - -20 ℃; for 0.5h; Molecular sieve;

DOI:10.1039/d0sc05862a

Reference yield:

C30H27N3O4S → 1,6-anhydro-4-O-[2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose (1415973-62-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: borane-THF; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 6 h / 0 °C

1.2: 12 h / 0 °C

2.1: trimethylsilyl trifluoromethanesulfonate; N-iodo-succinimide / dichloromethane / 0.5 h / -78 - -20 °C / Molecular sieve

With N-iodo-succinimide; borane-THF; trimethylsilyl trifluoromethanesulfonate; In dichloromethane;

DOI:10.1039/d0sc05862a

upstream raw materials:

4-methylphenyl 2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-1-thio-α/β-D-glucopyranoside

1,6-anhydro-2-O-benzoyl-3-O-benzyl-β-L-idopyranoside

tert-butylchlorodiphenylsilane

Downstream raw materials:

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