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

Base Information

• Chemical Name: methyl [phenyl 4-O-(2-azido-3,6-O-dibenzyl-2-deoxy-4-O-trichloroacetyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-1-thio-L-idopyranoside]uronate
• CAS No.: 1394857-52-3
• Molecular Formula: C₄₉H₄₆Cl₃N₃O₁₂S
• Molecular Weight: 1007.34

Synonyms:

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

There total 14 articles about methyl [phenyl 4-O-(2-azido-3,6-O-dibenzyl-2-deoxy-4-O-trichloroacetyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-1-thio-L-idopyranoside]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:

methyl (phenyl 2-O-benzoyl-3-O-benzyl-1-thio-L-idopyranoside)uronate (1178888-21-5) + 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-trichloroacetyl-1-O-trichloroacetimidate-α/β-D-glucopyranoside (1394857-41-0) → methyl [phenyl 4-O-(2-azido-3,6-O-dibenzyl-2-deoxy-4-O-trichloroacetyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-1-thio-L-idopyranoside]uronate (1394857-52-3) + 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 (1394857-53-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -30 ℃; for 1.25h; Overall yield = 41 %; Overall yield = 4.11 g; Inert atmosphere;

DOI:10.1021/jo300722y

Reference yield:

(+)-D-glucosamine hydrochloride (1078691-95-8) → methyl [phenyl 4-O-(2-azido-3,6-O-dibenzyl-2-deoxy-4-O-trichloroacetyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-1-thio-L-idopyranoside]uronate (1394857-52-3) + 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 (1394857-53-4)

Guidance literature:

Multi-step reaction with 12 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: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

10.1: N-Bromosuccinimide / acetone / 0 °C

11.1: sodium hydride / dichloromethane / 0.75 h

12.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1.25 h / -30 °C / Inert atmosphere

With pyridine; triethylsilane; imidazole-1-sulfonyl azide hydrochloride; N-Bromosuccinimide; copper(ll) sulfate pentahydrate; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; water; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetone; acetonitrile;

DOI:10.1021/jo300722y

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroacetamido)-β-D-glucopyranose (56644-75-8,10353-00-1) → methyl [phenyl 4-O-(2-azido-3,6-O-dibenzyl-2-deoxy-4-O-trichloroacetyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-1-thio-L-idopyranoside]uronate (1394857-52-3) + 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 (1394857-53-4)

Guidance literature:

Multi-step reaction with 10 steps

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

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

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

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

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

5.2: 3 h / 50 °C

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

7.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

8.1: N-Bromosuccinimide / acetone / 0 °C

9.1: sodium hydride / dichloromethane / 0.75 h

10.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1.25 h / -30 °C / Inert atmosphere

With triethylsilane; imidazole-1-sulfonyl azide hydrochloride; N-Bromosuccinimide; copper(ll) sulfate pentahydrate; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; water; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetone; acetonitrile;

DOI:10.1021/jo300722y

upstream raw materials:

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

methyl (phenyl 2-O-benzoyl-3-O-benzyl-1-thio-L-idopyranoside)uronate

2-azido-3,6-di-O-benzyl-2-deoxy-4-O-trichloroacetyl-1-O-trichloroacetimidate-α/β-D-glucopyranoside

(+)-D-glucosamine hydrochloride

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 1394857-52-3 methyl [phenyl 4-O-(2-azido-3,6-O-dibenzyl-2-deoxy-4-O-trichloroacetyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-1-thio-L-idopyranoside]uronate

Send

Send

Metric Ton KG G Pound L ML

Send

Send