methyl 4,6-O-benzylidene-2-deoxy-3-O-(phenylcarbamoyl)-2-phthalimido-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:methyl 4,6-O-benzylidene-2-deoxy-3-O-(phenylcarbamoyl)-2-phthalimido-1-thio-β-D-glucopyranoside
CAS No.:139525-93-2
Molecular Formula:C₂₉H₂₆N₂O₇S
Molecular Weight:546.601
Hs Code.:

Synonyms:methyl 4,6-O-benzylidene-2-deoxy-3-O-(phenylcarbamoyl)-2-phthalimido-1-thio-β-D-glucopyranoside

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Chemical Property of methyl 4,6-O-benzylidene-2-deoxy-3-O-(phenylcarbamoyl)-2-phthalimido-1-thio-β-D-glucopyranoside

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Technology Process of methyl 4,6-O-benzylidene-2-deoxy-3-O-(phenylcarbamoyl)-2-phthalimido-1-thio-β-D-glucopyranoside

There total 1 articles about methyl 4,6-O-benzylidene-2-deoxy-3-O-(phenylcarbamoyl)-2-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: 99.0%

: 103-71-9
phenyl isocyanate

: 139627-56-8
Methyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 139525-93-2
methyl 4,6-O-benzylidene-2-deoxy-3-O-(phenylcarbamoyl)-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: With pyridine; dmap; In 1,2-dichloro-ethane; at 50 ℃; for 4h;
DOI:10.1021/jo00032a601

Reference yield: 72.0%

: 139525-93-2
methyl 4,6-O-benzylidene-2-deoxy-3-O-(phenylcarbamoyl)-2-phthalimido-1-thio-β-D-glucopyranoside

: 139525-95-4
methyl 6-O-benzyl-2-deoxy-3-O-(phenylcarbamoyl)-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: With aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; In tetrahydrofuran; for 18h; Ambient temperature;
DOI:10.1021/jo00032a601

Reference yield:

: 139525-93-2
methyl 4,6-O-benzylidene-2-deoxy-3-O-(phenylcarbamoyl)-2-phthalimido-1-thio-β-D-glucopyranoside

: 139526-05-9
benzyl O-(3,4-di-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-(1->4)-2,3-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 72 percent / BH₃*Me₃N, AlCl₃, molecular sieve 4A / tetrahydrofuran / 18 h / Ambient temperature

2: 82 percent / Et₂NSF₃ / tetrahydrofuran / 5 h / 50 °C

3: 94 percent / 1M NaOMe / CH₂Cl₂; methanol / 1 h / 0 °C

4: 99 percent / pyridine, 4-dimethylaminopyridine / CH₂Cl₂ / 18 h / Ambient temperature

5: 99 percent / N-iodosuccinimide, molecular sieve 5A, TFA / toluene / 1.5 h / -40 to -10 deg C

With pyridine; dmap; N-iodo-succinimide; aluminium trichloride; diethylamino-sulfur trifluoride; trimethylamine-borane; 4 A molecular sieve; 5A molecular sieve; sodium methylate; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1021/jo00032a601