6-azidohexyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

• Chemical Name: 6-azidohexyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS No.: 651007-96-4
• Molecular Formula: C₃₆H₄₄N₄O₇Si
• Molecular Weight: 672.853

Synonyms:6-azidohexyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property of 6-azidohexyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property:

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Technology Process of 6-azidohexyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 2 articles about 6-azidohexyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 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%

tert-butylchlorodiphenylsilane (58479-61-1) + 6-azidohexyl 2-deoxy-2-phthalimido-β-D-glucopyranoside (651007-95-3) → 6-azidohexyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (651007-96-4)

Guidance literature:

With pyridine; dmap; triethylamine; In dichloromethane; for 16h;

DOI:10.1016/S0008-6215(03)00313-6

Reference yield:

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-O-trichloroacetimidate (87190-67-8) → 6-azidohexyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (651007-96-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / BF₃*Et₂O / CH₂Cl₂ / 3 h / 0 °C

2: 100 percent / NaOMe / methanol; CH₂Cl₂ / 5 h / pH 8

3: 88 percent / pyridine; 4-dimethylaminopyridine; Et₃N / CH₂Cl₂ / 16 h

With pyridine; dmap; boron trifluoride diethyl etherate; sodium methylate; triethylamine; In methanol; dichloromethane;

DOI:10.1016/S0008-6215(03)00313-6

Reference yield: 69.0%

4-methyl-benzoyl chloride (874-60-2) + 6-azidohexyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (651007-96-4) → 6-azidohexyl 6-O-tert-butyldiphenylsilyl-2-deoxy-3,4-di-O-methylbenzoyl-2-phthalimido-β-D-glucopyranoside (651007-97-5)

Guidance literature:

In pyridine; dichloromethane; at 0 ℃; for 20h;

DOI:10.1016/S0008-6215(03)00313-6

upstream raw materials:

tert-butylchlorodiphenylsilane

6-azidohexyl 2-deoxy-2-phthalimido-β-D-glucopyranoside

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-O-trichloroacetimidate

Downstream raw materials:

6-azidohexyl 6-O-tert-butyldiphenylsilyl-2-deoxy-3,4-di-O-methylbenzoyl-2-phthalimido-β-D-glucopyranoside

6-azidohexyl 2-deoxy-3,4-di-O-p-methylbenzoyl-2-phthalimido-β-D-glucopyranoside

6-azidohexyl (2,6-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->6)-2-deoxy-3,4-di-O-p-methylbenzoyl-2-phthalimido-β-D-glucopyranoside

6-azidohexyl (2,6-di-O-acetyl-3,4-di-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->6)-2-deoxy-3,4-di-O-p-methylbenzoyl-2-phthalimido-β-D-glucopyranoside

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