2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl trichloroacetimidate
• CAS No.: 229954-89-6
• Molecular Formula: C₄₄H₄₅Cl₃N₂O₁₆
• Molecular Weight: 964.204
• Mol file: 229954-89-6.mol

Synonyms:2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl trichloroacetimidate

Chemical Property of 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl trichloroacetimidate

There total 7 articles about 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl trichloroacetimidate 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: 88.0%

trichloroacetonitrile (545-06-2) + Acetic acid (2R,3R,4R,5R,6R)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxy-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester → 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl trichloroacetimidate (229954-89-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/S0008-6215(99)00018-X

Reference yield:

ethyl 2,3,4-tri-O-acetyl-6-O-benzyl-1-thio-β-D-galactopyranoside (107855-14-1) → 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl trichloroacetimidate (229954-89-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 74 percent / powdered 4 Angstroem molecular sieves; NIS; TfOH / CH₂Cl₂ / 1 h / -40 °C

2: 79 percent / powdered 3 Angstroem molecular sieves; sodium cyanoborohydride; HCl / tetrahydrofuran; diethyl ether / 2 h / 0 °C / pH 3

3: pyridine / CH₂Cl₂ / 4 h / 20 °C

4: 89 percent / dimethylformamide / 2 h / 20 °C

5: TFA / CH₂Cl₂ / 1 h / 20 °C

6: 88 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 2 h / 0 °C

With pyridine; hydrogenchloride; N-iodo-succinimide; trifluorormethanesulfonic acid; 3 A molecular sieve; 4 A molecular sieve; sodium cyanoborohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Alkylation / 2: Hydrolysis / 3: Esterification / 4: transesterification / 5: acidolysis / 6: Substitution;

DOI:10.1016/S0008-6215(99)00018-X

Reference yield:

2-(trimethylsilyl)ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (174392-90-6) → 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl trichloroacetimidate (229954-89-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 74 percent / powdered 4 Angstroem molecular sieves; NIS; TfOH / CH₂Cl₂ / 1 h / -40 °C

2: 79 percent / powdered 3 Angstroem molecular sieves; sodium cyanoborohydride; HCl / tetrahydrofuran; diethyl ether / 2 h / 0 °C / pH 3

3: pyridine / CH₂Cl₂ / 4 h / 20 °C

4: 89 percent / dimethylformamide / 2 h / 20 °C

5: TFA / CH₂Cl₂ / 1 h / 20 °C

6: 88 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 2 h / 0 °C

With pyridine; hydrogenchloride; N-iodo-succinimide; trifluorormethanesulfonic acid; 3 A molecular sieve; 4 A molecular sieve; sodium cyanoborohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Alkylation / 2: Hydrolysis / 3: Esterification / 4: transesterification / 5: acidolysis / 6: Substitution;

DOI:10.1016/S0008-6215(99)00018-X

upstream raw materials:

trichloroacetonitrile

ethyl 2,3,4-tri-O-acetyl-6-O-benzyl-1-thio-β-D-galactopyranoside

2-(trimethylsilyl)ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

2-trimethylsilylethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside