phenyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

Base Information

Chemical Name:phenyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside
CAS No.:204199-43-9
Molecular Formula:C₃₈H₄₁N₃O₁₂S
Molecular Weight:763.822
Hs Code.:

Synonyms:phenyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

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Chemical Property of phenyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

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Technology Process of phenyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

There total 5 articles about phenyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside 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: 64.0%

: 67817-16-7
3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-glucopyranosyl chloride

: 204199-42-8
phenyl 2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

: 204199-43-9
phenyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

Guidance literature:: With 2,6-di-tert-butyl-4-methylpyridine; silver trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1002/(sici)1521-3773(19980202)37:1/2<138::aid-anie138>3.0.co;2-t

Reference yield:

: 100-39-0
benzyl bromide

: 204199-43-9
phenyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / dimethylformamide / 2 h / 0 °C

2.1: 63.5 g / aq. AcOH / 3 h / 90 °C

3.1: 10-camphorsulfonic acid / CH₂Cl₂ / 1 h / 23 °C

3.2: 92 percent / aq. AcOH / 0.17 h

4.1: 63.5 percent / 2,6-di-tert-butyl-4-methylpyridine; 4-Angstroem molecular sieves; silver trifluoromethanesulfonate / CH₂Cl₂ / 2 h / -20 - 0 °C

With 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; (1S)-10-camphorsulfonic acid; silver trifluoromethanesulfonate; sodium hydride; acetic acid; In dichloromethane; N,N-dimethyl-formamide; 1.1: Etherification / 2.1: Hydrolysis / 3.1: Esterification / 3.2: Hydrolysis / 4.1: Condensation;
DOI:10.1021/jo980660a

Reference yield:

: 131087-35-9
phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

: 204199-43-9
phenyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / dimethylformamide / 2 h / 0 °C

2.1: 63.5 g / aq. AcOH / 3 h / 90 °C

3.1: 10-camphorsulfonic acid / CH₂Cl₂ / 1 h / 23 °C

3.2: 92 percent / aq. AcOH / 0.17 h

4.1: 63.5 percent / 2,6-di-tert-butyl-4-methylpyridine; 4-Angstroem molecular sieves; silver trifluoromethanesulfonate / CH₂Cl₂ / 2 h / -20 - 0 °C

With 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; (1S)-10-camphorsulfonic acid; silver trifluoromethanesulfonate; sodium hydride; acetic acid; In dichloromethane; N,N-dimethyl-formamide; 1.1: Etherification / 2.1: Hydrolysis / 3.1: Esterification / 3.2: Hydrolysis / 4.1: Condensation;
DOI:10.1021/jo980660a