3-(trifluoroacetamido)propyl 2-acetamido-6-O-benzyl-3-O-(6-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: 3-(trifluoroacetamido)propyl 2-acetamido-6-O-benzyl-3-O-(6-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside
• CAS No.: 121042-79-3
• Molecular Formula: C₃₆H₄₇F₃N₂O₁₂
• Molecular Weight: 756.771
• Mol file: 121042-79-3.mol

Synonyms:

Chemical Property of 3-(trifluoroacetamido)propyl 2-acetamido-6-O-benzyl-3-O-(6-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(trifluoroacetamido)propyl 2-acetamido-6-O-benzyl-3-O-(6-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside

There total 12 articles about 3-(trifluoroacetamido)propyl 2-acetamido-6-O-benzyl-3-O-(6-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2-deoxy-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:

N-{3-[(2R,3R,4R,5S)-3-Acetylamino-6-benzyloxymethyl-4-((2R,3R,4S,5R,6R)-6-benzyloxymethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-5-hydroxy-tetrahydro-pyran-2-yloxy]-propyl}-2,2,2-trifluoro-acetamide + 2,2-dimethoxy-propane (77-76-9) → 3-(trifluoroacetamido)propyl 2-acetamido-6-O-benzyl-3-O-(6-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside (121042-79-3)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 0.166667h; Yield given;

DOI:10.1007/BF00598177

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 3-(trifluoroacetamido)propyl 2-acetamido-6-O-benzyl-3-O-(6-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside (121042-79-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 1) CH₃ONa, 2) toluene-4-sulfonic acid / 1) CH₃OH, 2 h, 2) CH₃CN, 50 deg C

2: pyridine / 20 h

3: NaBH₃CN, HCl / tetrahydrofuran; diethyl ether / 8 h / 20 °C / molecular sieve 3 Angstroem

4: CH₃ONa / methanol / 24 h

5: mercury cyanide / nitromethane; benzene / 2 h / 50 - 60 °C / molecular sieve 4 Angstroem

6: CH₃ONa / methanol / 15 h

7: toluene-4-sulfonic acid / acetonitrile / 0.5 h / 50 °C

8: pyridine / 15 h

9: 1) NaBH₃CN, 2) HCl / 1) THF, molecular sieve 3 Angstroem, 2 h, 2) ether, 8 h

10: CH₃ONa / methanol / 15 h

11: toluene-4-sulfonic acid / CH₂Cl₂ / 0.17 h / 20 °C

With pyridine; hydrogenchloride; sodium methylate; mercury(II) cyanide; sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; nitromethane; dichloromethane; acetonitrile; benzene;

DOI:10.1007/BF00598177

Reference yield:

3-(trifluoroacetamido)propyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (121042-71-5) → 3-(trifluoroacetamido)propyl 2-acetamido-6-O-benzyl-3-O-(6-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside (121042-79-3)

Guidance literature:

Multi-step reaction with 10 steps

1: pyridine / 20 h

2: NaBH₃CN, HCl / tetrahydrofuran; diethyl ether / 8 h / 20 °C / molecular sieve 3 Angstroem

3: CH₃ONa / methanol / 24 h

4: mercury cyanide / nitromethane; benzene / 2 h / 50 - 60 °C / molecular sieve 4 Angstroem

5: CH₃ONa / methanol / 15 h

6: toluene-4-sulfonic acid / acetonitrile / 0.5 h / 50 °C

7: pyridine / 15 h

8: 1) NaBH₃CN, 2) HCl / 1) THF, molecular sieve 3 Angstroem, 2 h, 2) ether, 8 h

9: CH₃ONa / methanol / 15 h

10: toluene-4-sulfonic acid / CH₂Cl₂ / 0.17 h / 20 °C

With pyridine; hydrogenchloride; sodium methylate; mercury(II) cyanide; sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; nitromethane; dichloromethane; acetonitrile; benzene;

DOI:10.1007/BF00598177

upstream raw materials:

2,2-dimethoxy-propane

benzaldehyde dimethyl acetal

3-trifluoroacetamidopropyl 2-acetamido-6-O-benzyl-2-deoxy-β-D-glucopyranoside

3-(trifluoroacetamido)propyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Downstream raw materials:

C₆₃H₇₅F₃N₂O₁₆

3-(trifluoroacetamido)propyl 2-acetamido-6-O-benzyl-3-O-<6-O-benzyl-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-3,4-O-isopropylidene-β-D-galactopyranosyl>-4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside