p-tolyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: p-tolyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 807361-23-5
• Molecular Formula: C₃₅H₃₃NO₆S
• Molecular Weight: 595.716

Synonyms:p-tolyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property of p-tolyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property:

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Technology Process of p-tolyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside

There total 9 articles about p-tolyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-1-thio-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: 90.0%

p-tolyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (501089-70-9) → p-tolyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside (807361-23-5)

Guidance literature:

With hydrogenchloride; 3 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; at 20 ℃; for 0.166667h;

DOI:10.1021/ol0483246

Reference yield:

4-methylphenyl 4,6-O-benzylidene-2-deoxyl-1-thio-2-phthalimido-β-D-glucopyranoside (220645-16-9) → p-tolyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside (807361-23-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / tetrabutylammonium iodide; 4 Angstroem molecular sieves; NaH / dimethylformamide / 2 h / 0 - 20 °C

2: 90 percent / NaCNBH₃; HCl; molecular sieves AW₃₀₀ / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

With hydrogenchloride; 3 A molecular sieve; 4 A molecular sieve; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2006.01.007

Reference yield:

benzyl bromide (100-39-0) → p-tolyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside (807361-23-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / NaH / dimethylformamide / 0 - 20 °C

2: 90 percent / HCl*Et₂O; NaCNBH₃ / tetrahydrofuran / 20 °C

With hydrochloric acid diethyl ether; sodium hydride; sodium cyanoborohydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2005.02.023

upstream raw materials:

p-tolyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

benzyl bromide

4-methylphenyl 4,6-O-benzylidene-2-deoxyl-1-thio-2-phthalimido-β-D-glucopyranoside

phthalic anhydride

Downstream raw materials:

p-tolyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

p-tolyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-α-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

C₄₉H₅₁NO₁₅S

C₄₁H₄₇NO₆SSi

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