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

Base Information

• Chemical Name: p-methylphenyl 2-azido-2-deoxy-4-O-(2-naphthylmethyl)-1-thio-D-glucopyranoside ⁽⁴⁾
• CAS No.: 1314746-20-7
• Molecular Formula: C₂₄H₂₅N₃O₄S
• Molecular Weight: 451.546

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

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

Chemical Property:

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

There total 3 articles about p-methylphenyl 2-azido-2-deoxy-4-O-(2-naphthylmethyl)-1-thio-D-glucopyranoside ⁽⁴⁾ 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: 88.0%

4-methylphenyl 2-azido-2-deoxy-1-thio-α,β-D-glucopyranoside + β-naphthaldehyde (66-99-9) → p-methylphenyl 2-azido-2-deoxy-4-O-(2-naphthylmethyl)-1-thio-D-glucopyranoside (4) (1314746-20-7)

Guidance literature:

4-methylphenyl 2-azido-2-deoxy-1-thio-α,β-D-glucopyranoside; With trimethylsilyl trifluoromethanesulfonate; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane; for 1h;

β-naphthaldehyde; In dichloromethane; for 1h; Further stages; Molecular sieve;

Reference yield: 77.0%

C22H41N3O4SSi3 (1314746-19-4) + β-naphthaldehyde (66-99-9) → p-methylphenyl 2-azido-2-deoxy-4-O-(2-naphthylmethyl)-1-thio-D-glucopyranoside (4) (1314746-20-7)

Guidance literature:

C₂₂H₄₁N₃O₄SSi₃; β-naphthaldehyde; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; for 2h;

With borane-THF; trimethylsilyl trifluoromethanesulfonate; In dichloromethane;

DOI:10.1038/nchem.1073

Reference yield:

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose (171032-74-9) → p-methylphenyl 2-azido-2-deoxy-4-O-(2-naphthylmethyl)-1-thio-D-glucopyranoside (4) (1314746-20-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: boron trifluoride diethyl etherate / 8 h / 20 °C

1.2: 16 h / Reflux

2.1: trimethylsilyl trifluoromethanesulfonate; 1,1,1,3,3,3-hexamethyl-disilazane / dichloromethane / 1 h

2.2: 1 h / Molecular sieve

With trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane;

upstream raw materials:

C₂₂H₄₁N₃O₄SSi₃

β-naphthaldehyde

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose

Downstream raw materials:

p-methylphenyl 2-azido-3-O-(p-bromobenzyl)-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 trichloroacetimidate

C₅₈H₆₄BrN₃O₁₅Si

C₅₈H₆₂BrCl₃N₄O₁₄Si

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