(5-N-benzyloxyacetamido-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosyl)onate-(2→3)-p-toluyl-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: (5-N-benzyloxyacetamido-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosyl)onate-(2→3)-p-toluyl-1-thio-β-D-galactopyranoside
• CAS No.: 1453169-48-6
• Molecular Formula: C₃₁H₄₁NO₁₄S
• Molecular Weight: 683.731
• Mol file: 1453169-48-6.mol

Synonyms:

Chemical Property of (5-N-benzyloxyacetamido-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosyl)onate-(2→3)-p-toluyl-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5-N-benzyloxyacetamido-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosyl)onate-(2→3)-p-toluyl-1-thio-β-D-galactopyranoside

There total 7 articles about (5-N-benzyloxyacetamido-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosyl)onate-(2→3)-p-toluyl-1-thio-β-D-galactopyranoside 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:

C22H33NO12S + O-benzylglycolic acid succinimidyl ester (71624-31-2) → (5-N-benzyloxyacetamido-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosyl)onate-(2→3)-p-toluyl-1-thio-β-D-galactopyranoside (1453169-48-6)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 0 ℃; for 5h; Inert atmosphere;

DOI:10.1002/ejoc.201300664

Reference yield:

methyl (5-tert-butyloxycabonyl-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosyl)onate-(2→3)-p-toluyl-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (1453169-44-2) → (5-N-benzyloxyacetamido-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosyl)onate-(2→3)-p-toluyl-1-thio-β-D-galactopyranoside (1453169-48-6)

Guidance literature:

Multi-step reaction with 4 steps

1: camphor-10-sulfonic acid / methanol / 16 h / 20 °C / Inert atmosphere

2: potassium tert-butylate / tetrahydrofuran; methanol / 16 h / 20 °C / Inert atmosphere

3: trifluoroacetic acid / dichloromethane / 0.17 h / 20 °C / Inert atmosphere

4: triethylamine / N,N-dimethyl-formamide / 5 h / 0 °C / Inert atmosphere

With camphor-10-sulfonic acid; potassium tert-butylate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201300664

Reference yield:

methyl (5-tert-butyloxycarbonyl-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-2-thiotoluyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranoside)onate (1453169-69-1) → (5-N-benzyloxyacetamido-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosyl)onate-(2→3)-p-toluyl-1-thio-β-D-galactopyranoside (1453169-48-6)

Guidance literature:

Multi-step reaction with 6 steps

1: N-iodo-succinimide; trifluorormethanesulfonic acid / dichloromethane / 5 h / 0 °C / Molecular sieve; Inert atmosphere

2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -78 °C / Inert atmosphere; Molecular sieve

3: camphor-10-sulfonic acid / methanol / 16 h / 20 °C / Inert atmosphere

4: potassium tert-butylate / tetrahydrofuran; methanol / 16 h / 20 °C / Inert atmosphere

5: trifluoroacetic acid / dichloromethane / 0.17 h / 20 °C / Inert atmosphere

6: triethylamine / N,N-dimethyl-formamide / 5 h / 0 °C / Inert atmosphere

With N-iodo-succinimide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; potassium tert-butylate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201300664

upstream raw materials:

methyl (5-tert-butyloxycabonyl-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosyl)onate-(2→3)-p-toluyl-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

methyl (5-tert-butyloxycarbonyl-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-2-thiotoluyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranoside)onate

O-benzylglycolic acid succinimidyl ester

C₂₇H₄₁NO₁₄S