phenyl 5-amino-4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam

Base Information

Chemical Name:phenyl 5-amino-4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam
CAS No.:872120-66-6
Molecular Formula:C₂₆H₂₉NO₈S
Molecular Weight:515.584
Hs Code.:

Synonyms:phenyl 5-amino-4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam

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Chemical Property of phenyl 5-amino-4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam

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Technology Process of phenyl 5-amino-4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam

There total 7 articles about phenyl 5-amino-4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam 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: 74.0%

: 872120-65-5
phenyl 4,7-di-O-acetyl-5-amino-9-O-benzylidene-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam

: 872120-66-6
phenyl 5-amino-4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam

Guidance literature:: With aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; In tetrahydrofuran; at 0 - 20 ℃; for 6h;
DOI:10.1016/j.carres.2006.03.017

Reference yield:

: methyl (phenyl 3,5-dideoxy-2-thio-5-trifluoroacetamido-D-glycero-α-D-galacto-nonulopyranosid)onate

: 872120-66-6
phenyl 5-amino-4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam

Guidance literature:: Multi-step reaction with 5 steps

1: 230 mg / camphorsulfonic acid / dimethylformamide / 2 h / 40 °C

2: 89 percent / sodium methoxide; Drierite / methanol / 120 h / Heating

3: pyridine; 4-dimethylaminopyridine / 3 h / 20 °C

4: 1.38 g / hydrazinium acetate / tetrahydrofuran / 1.33 h / 20 °C

5: 74 percent / BH₃*NMe₃; AlCl₃; molecular sieves 4 Angstroem / tetrahydrofuran / 6 h / 0 - 20 °C

With pyridine; dmap; calcium sulfate; aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; camphor-10-sulfonic acid; sodium methylate; hydrazinium monoacetate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1002/anie.200501608

Reference yield:

: 872120-63-3
methyl (phenyl 8,9-O-benzylidene-3,5-dideoxy-2-thio-5-trifluoroacetamido-D-glycero-α-D-galacto-2-nonulopyranosid)onate

: 872120-66-6
phenyl 5-amino-4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / sodium methoxide; Drierite / methanol / 120 h / Heating

2: pyridine; 4-dimethylaminopyridine / 3 h / 20 °C

3: 1.38 g / hydrazinium acetate / tetrahydrofuran / 1.33 h / 20 °C

4: 74 percent / BH₃*NMe₃; AlCl₃; molecular sieves 4 Angstroem / tetrahydrofuran / 6 h / 0 - 20 °C

With pyridine; dmap; calcium sulfate; aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; sodium methylate; hydrazinium monoacetate; In tetrahydrofuran; methanol;
DOI:10.1002/anie.200501608