phenyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-glucopyranosyl(1->3)-2-O-benzoyl-4,6-O-[(R)-1-(methoxycarbonyl)ethylidene]-1-thio-β-D-galactopyranoside

Base Information

Chemical Name:phenyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-glucopyranosyl(1->3)-2-O-benzoyl-4,6-O-[(R)-1-(methoxycarbonyl)ethylidene]-1-thio-β-D-galactopyranoside
CAS No.:653572-82-8
Molecular Formula:C₅₂H₄₉NO₁₆S
Molecular Weight:976.024
Hs Code.:

phenyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-glucopyranosyl(1->3)-2-O-benzoyl-4,6-O-[(R)-1-(methoxycarbonyl)ethylidene]-1-thio-β-D-galactopyranoside

Synonyms:phenyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-glucopyranosyl(1->3)-2-O-benzoyl-4,6-O-[(R)-1-(methoxycarbonyl)ethylidene]-1-thio-β-D-galactopyranoside

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Chemical Property of phenyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-glucopyranosyl(1->3)-2-O-benzoyl-4,6-O-[(R)-1-(methoxycarbonyl)ethylidene]-1-thio-β-D-galactopyranoside

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Technology Process of phenyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-glucopyranosyl(1->3)-2-O-benzoyl-4,6-O-[(R)-1-(methoxycarbonyl)ethylidene]-1-thio-β-D-galactopyranoside

There total 13 articles about phenyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-glucopyranosyl(1->3)-2-O-benzoyl-4,6-O-[(R)-1-(methoxycarbonyl)ethylidene]-1-thio-β-D-galactopyranoside 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: 45.0%

: 600-22-6
pyruvic acid methyl ester

: 653572-81-7
phenyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-glucopyranosyl(1->3)-2-O-benzoyl-1-thio-β-D-galactopyranoside

: 653572-82-8
phenyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-glucopyranosyl(1->3)-2-O-benzoyl-4,6-O-[(R)-1-(methoxycarbonyl)ethylidene]-1-thio-β-D-galactopyranoside

: phenyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-glucopyranosyl(1->3)-2-O-benzoyl-4,6-O-[(S)-1-(methoxycarbonyl)ethylidene]-1-thio-β-D-galactopyranoside

Guidance literature:: With boron trifluoride diethyl etherate; In acetonitrile; at 20 ℃; for 3h;
DOI:10.1081/CAR-120026456

Reference yield:

: 16758-34-2
1-thiophenyl-β-D-galactopyranoside

: 653572-82-8
phenyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-glucopyranosyl(1->3)-2-O-benzoyl-4,6-O-[(R)-1-(methoxycarbonyl)ethylidene]-1-thio-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 13 steps

1: 73 percent / pyridine / 3 h / 25 °C

2: 77.9 percent / 10-camphorsulfonic acid / dimethylformamide / 12 h / 20 °C

3: 93 percent / pyridine / 3 h

4: 92 percent / acetic acid / 1 h / 80 °C

5: 71 percent / molecular sieves 4 Angstroem; TESOTf / CH₂Cl₂ / 0.5 h / -30 °C

6: 74 percent / Bu₄NF / tetrahydrofuran / 6 h / 0 - 25 °C

7: 88 percent / 10-camphorsulfonic acid / acetonitrile / 2 h / 20 °C

8: ethylenediamine / butan-1-ol / 20 h / 90 °C

9: pyridine / 14 h / 20 °C

10: 100 percent / NaOMe / methanol / 1 h / 25 °C

11: 93 percent / pyridine / 4 h / 0 °C

12: 81 percent / acetic acid / 1 h / 70 °C

13: 45 percent / BF₃*Et₂O / acetonitrile / 3 h / 20 °C

With pyridine; 4 A molecular sieve; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; triethylsilyl trifluoromethyl sulfonate; sodium methylate; acetic acid; ethylenediamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; butan-1-ol;
DOI:10.1081/CAR-120026456

Reference yield:

: 195316-81-5
phenyl 6-O-(tert-butyl(diphenyl)silyl)-1-thio-β-D-galactopyranoside

: 653572-82-8
phenyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-glucopyranosyl(1->3)-2-O-benzoyl-4,6-O-[(R)-1-(methoxycarbonyl)ethylidene]-1-thio-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 12 steps

1: 77.9 percent / 10-camphorsulfonic acid / dimethylformamide / 12 h / 20 °C

2: 93 percent / pyridine / 3 h

3: 92 percent / acetic acid / 1 h / 80 °C

4: 71 percent / molecular sieves 4 Angstroem; TESOTf / CH₂Cl₂ / 0.5 h / -30 °C

5: 74 percent / Bu₄NF / tetrahydrofuran / 6 h / 0 - 25 °C

6: 88 percent / 10-camphorsulfonic acid / acetonitrile / 2 h / 20 °C

7: ethylenediamine / butan-1-ol / 20 h / 90 °C

8: pyridine / 14 h / 20 °C

9: 100 percent / NaOMe / methanol / 1 h / 25 °C

10: 93 percent / pyridine / 4 h / 0 °C

11: 81 percent / acetic acid / 1 h / 70 °C

12: 45 percent / BF₃*Et₂O / acetonitrile / 3 h / 20 °C

With pyridine; 4 A molecular sieve; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; triethylsilyl trifluoromethyl sulfonate; sodium methylate; acetic acid; ethylenediamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; butan-1-ol;
DOI:10.1081/CAR-120026456