Phenyl [methyl (N-acetyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-nonulopyranosyl)onate]-(2->3)-(6-O-pivaloyl-2,4-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2-deoxy-6-O-naphthylmethyl-2-phthalimido-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: Phenyl [methyl (N-acetyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-nonulopyranosyl)onate]-(2->3)-(6-O-pivaloyl-2,4-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2-deoxy-6-O-naphthylmethyl-2-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 329783-76-8
• Molecular Formula: C₆₈H₇₈N₂O₂₇S
• Molecular Weight: 1387.43
• Mol file: 329783-76-8.mol

Synonyms:Phenyl [methyl (N-acetyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-nonulopyranosyl)onate]-(2->3)-(6-O-pivaloyl-2,4-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2-deoxy-6-O-naphthylmethyl-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property of Phenyl [methyl (N-acetyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-nonulopyranosyl)onate]-(2->3)-(6-O-pivaloyl-2,4-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2-deoxy-6-O-naphthylmethyl-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phenyl [methyl (N-acetyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-nonulopyranosyl)onate]-(2->3)-(6-O-pivaloyl-2,4-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2-deoxy-6-O-naphthylmethyl-2-phthalimido-1-thio-β-D-glucopyranoside

There total 9 articles about Phenyl [methyl (N-acetyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-nonulopyranosyl)onate]-(2->3)-(6-O-pivaloyl-2,4-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2-deoxy-6-O-naphthylmethyl-2-phthalimido-1-thio-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: 87.0%

phenyl 6-O-(2-naphthylmethyl)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (260411-26-5) + [Methyl (N-acetyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onate]-(2->3)-6-O-pivaloyl-2,4-di-O-acetyl-β-D-galactopyranosyl trichloroacetimidate (329783-81-5) → Phenyl [methyl (N-acetyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-nonulopyranosyl)onate]-(2->3)-(6-O-pivaloyl-2,4-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2-deoxy-6-O-naphthylmethyl-2-phthalimido-1-thio-β-D-glucopyranoside (329783-76-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -45 - -40 ℃; for 1.5h;

DOI:10.1002/1521-3765(20010119)7:2<356::AID-CHEM356>3.0.CO;2-E

Reference yield:

Benzyl 3,4-O-isopropylidene-β-D-galactopyranoside (14897-51-9) → Phenyl [methyl (N-acetyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-nonulopyranosyl)onate]-(2->3)-(6-O-pivaloyl-2,4-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2-deoxy-6-O-naphthylmethyl-2-phthalimido-1-thio-β-D-glucopyranoside (329783-76-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 77 percent / pyridine / 12 h / 0 - 25 °C

2.1: 90 percent / aq. acetic acid / 1.5 h / 60 - 65 °C

3.1: NIS; 3 Angstroem molecular sieves / CH₂Cl₂; acetonitrile / 2 h / -65 - -60 °C

3.2: 66 percent / TfOH / CH₂Cl₂; acetonitrile / 6 h / -65 - -40 °C

4.1: 81 percent / pyridine; DMAP / 12 h / 20 °C

5.1: 1.29 g / H₂ / 10percent Pd/C / CH₂Cl₂; methanol / 24 h / 20 °C

6.1: 96 percent / DBU / CH₂Cl₂ / 2 h / 0 °C

7.1: 87 percent / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂ / 1.5 h / -45 - -40 °C

With pyridine; dmap; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; hydrogen; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 10percent Pd/C; In methanol; dichloromethane; acetonitrile;

DOI:10.1002/1521-3765(20010119)7:2<356::AID-CHEM356>3.0.CO;2-E

Reference yield:

Phenyl (methyl N-acetyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-β-thio-D-glycero-D-galacto-2-nonulopyranosid)onate → Phenyl [methyl (N-acetyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-nonulopyranosyl)onate]-(2->3)-(6-O-pivaloyl-2,4-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2-deoxy-6-O-naphthylmethyl-2-phthalimido-1-thio-β-D-glucopyranoside (329783-76-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NIS; 3 Angstroem molecular sieves / CH₂Cl₂; acetonitrile / 2 h / -65 - -60 °C

1.2: 66 percent / TfOH / CH₂Cl₂; acetonitrile / 6 h / -65 - -40 °C

2.1: 81 percent / pyridine; DMAP / 12 h / 20 °C

3.1: 1.29 g / H₂ / 10percent Pd/C / CH₂Cl₂; methanol / 24 h / 20 °C

4.1: 96 percent / DBU / CH₂Cl₂ / 2 h / 0 °C

5.1: 87 percent / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂ / 1.5 h / -45 - -40 °C

With pyridine; dmap; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; 10percent Pd/C; In methanol; dichloromethane; acetonitrile;

DOI:10.1002/1521-3765(20010119)7:2<356::AID-CHEM356>3.0.CO;2-E

upstream raw materials:

phenyl 6-O-(2-naphthylmethyl)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

[Methyl (N-acetyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onate]-(2->3)-6-O-pivaloyl-2,4-di-O-acetyl-β-D-galactopyranosyl trichloroacetimidate

Benzyl 3,4-O-isopropylidene-β-D-galactopyranoside

Benzyl 6-O-pivaloyl-β-D-galactopyranoside