methyl [phenyl 4-O-(2-azido-3,6-O-dibenzyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-1-thio-β-L-ido-pyranoside]uronate

Base Information

• Chemical Name: methyl [phenyl 4-O-(2-azido-3,6-O-dibenzyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-1-thio-β-L-ido-pyranoside]uronate
• CAS No.: 1394857-57-8
• Molecular Formula: C₄₇H₄₇N₃O₁₁S
• Molecular Weight: 861.97
• Mol file: 1394857-57-8.mol

Synonyms:methyl [phenyl 4-O-(2-azido-3,6-O-dibenzyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-1-thio-β-L-ido-pyranoside]uronate

Chemical Property of methyl [phenyl 4-O-(2-azido-3,6-O-dibenzyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-1-thio-β-L-ido-pyranoside]uronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl [phenyl 4-O-(2-azido-3,6-O-dibenzyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-1-thio-β-L-ido-pyranoside]uronate

There total 14 articles about methyl [phenyl 4-O-(2-azido-3,6-O-dibenzyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-1-thio-β-L-ido-pyranoside]uronate 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: 92.0%

methyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1→4)-(phenyl 3-O-benzyl-2-O-benzoyl-1-thio-β-L-idopyranoside)uronate (1394857-51-2) → methyl [phenyl 4-O-(2-azido-3,6-O-dibenzyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-1-thio-β-L-ido-pyranoside]uronate (1394857-57-8)

Guidance literature:

With ammonium cerium (IV) nitrate; water; In acetonitrile; for 2.5h; Inert atmosphere;

DOI:10.1021/jo300722y

Reference yield:

2-deoxy-2-trichloroacetamido-α/β-D-glucopyranose → methyl [phenyl 4-O-(2-azido-3,6-O-dibenzyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-1-thio-β-L-ido-pyranoside]uronate (1394857-57-8)

Guidance literature:

Multi-step reaction with 12 steps

1.1: pyridine / dichloromethane / 16 h / 0 - 20 °C

2.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 18 h / 20 °C / Inert atmosphere

3.1: potassium carbonate; water / methanol / 18 h / 60 °C

4.1: imidazole-1-sulfonyl azide hydrochloride; copper(ll) sulfate pentahydrate; potassium carbonate / methanol / 2.67 h / 20 °C

5.1: toluene-4-sulfonic acid / acetonitrile / 72 h / 20 °C

6.1: sodium hydride / tetrahydrofuran / 1.5 h / 20 °C

6.2: 3 h / 50 °C

7.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 4 h / 0 °C / Inert atmosphere

8.1: sodium hydride / tetrahydrofuran; mineral oil / 60 °C / Inert atmosphere

9.1: N-Bromosuccinimide / acetone / 0 °C

10.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / Inert atmosphere

11.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1.75 h / -30 °C / Inert atmosphere

12.1: ammonium cerium (IV) nitrate; water / acetonitrile / 2.5 h / Inert atmosphere

With pyridine; triethylsilane; imidazole-1-sulfonyl azide hydrochloride; N-Bromosuccinimide; copper(ll) sulfate pentahydrate; ammonium cerium (IV) nitrate; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; water; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane; acetone; acetonitrile; mineral oil;

DOI:10.1021/jo300722y

Reference yield:

(+)-D-glucosamine hydrochloride (1078691-95-8) → methyl [phenyl 4-O-(2-azido-3,6-O-dibenzyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-1-thio-β-L-ido-pyranoside]uronate (1394857-57-8)

Guidance literature:

Multi-step reaction with 13 steps

1.1: triethylamine / methanol / 20 °C

1.2: 5 h / 0 - 20 °C

2.1: pyridine / dichloromethane / 16 h / 0 - 20 °C

3.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 18 h / 20 °C / Inert atmosphere

4.1: potassium carbonate; water / methanol / 18 h / 60 °C

5.1: imidazole-1-sulfonyl azide hydrochloride; copper(ll) sulfate pentahydrate; potassium carbonate / methanol / 2.67 h / 20 °C

6.1: toluene-4-sulfonic acid / acetonitrile / 72 h / 20 °C

7.1: sodium hydride / tetrahydrofuran / 1.5 h / 20 °C

7.2: 3 h / 50 °C

8.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 4 h / 0 °C / Inert atmosphere

9.1: sodium hydride / tetrahydrofuran; mineral oil / 60 °C / Inert atmosphere

10.1: N-Bromosuccinimide / acetone / 0 °C

11.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / Inert atmosphere

12.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1.75 h / -30 °C / Inert atmosphere

13.1: ammonium cerium (IV) nitrate; water / acetonitrile / 2.5 h / Inert atmosphere

With pyridine; triethylsilane; imidazole-1-sulfonyl azide hydrochloride; N-Bromosuccinimide; copper(ll) sulfate pentahydrate; ammonium cerium (IV) nitrate; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; water; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetone; acetonitrile; mineral oil;

DOI:10.1021/jo300722y

upstream raw materials:

phenyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside

(+)-D-glucosamine hydrochloride

phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-trichloroacetamido-β-D-glucopyranoside

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroacetamido)-β-D-glucopyranose

Downstream raw materials:

methyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-trichloroacetyl-α-D-glucopyranosyl-(1→4)-(phenyl-2-O-benzoyl-3-O-benzyl-1-thio-β-L-idopyranoside)uronate