methyl 4-hydroxy-2,3,5-tri-O-methyl-α-D-arabinofuranosyl(1->4)-6-deoxy-2,3-di-O-methyl-6-(4-nitrophenylsulfonylamino)-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 4-hydroxy-2,3,5-tri-O-methyl-α-D-arabinofuranosyl(1->4)-6-deoxy-2,3-di-O-methyl-6-(4-nitrophenylsulfonylamino)-α-D-glucopyranoside
• CAS No.: 1356387-55-7
• Molecular Formula: C₂₃H₃₆N₂O₁₄S
• Molecular Weight: 596.61
• Mol file: 1356387-55-7.mol

Synonyms:methyl 4-hydroxy-2,3,5-tri-O-methyl-α-D-arabinofuranosyl(1->4)-6-deoxy-2,3-di-O-methyl-6-(4-nitrophenylsulfonylamino)-α-D-glucopyranoside

Chemical Property of methyl 4-hydroxy-2,3,5-tri-O-methyl-α-D-arabinofuranosyl(1->4)-6-deoxy-2,3-di-O-methyl-6-(4-nitrophenylsulfonylamino)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-hydroxy-2,3,5-tri-O-methyl-α-D-arabinofuranosyl(1->4)-6-deoxy-2,3-di-O-methyl-6-(4-nitrophenylsulfonylamino)-α-D-glucopyranoside

There total 6 articles about methyl 4-hydroxy-2,3,5-tri-O-methyl-α-D-arabinofuranosyl(1->4)-6-deoxy-2,3-di-O-methyl-6-(4-nitrophenylsulfonylamino)-α-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: 46.0%

methyl 2,3,5-tri-O-methyl-α-D-arabinofuranosyl(1->4)-6-deoxy-2,3-di-O-methyl-6-(4-nitrophenylsulfonylamino)-α-D-glucopyranoside (1356387-49-9) → methyl 4-hydroxy-2,3,5-tri-O-methyl-α-D-arabinofuranosyl(1->4)-6-deoxy-2,3-di-O-methyl-6-(4-nitrophenylsulfonylamino)-α-D-glucopyranoside (1356387-55-7)

Guidance literature:

With [bis(acetoxy)iodo]benzene; iodine; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere; Irradiation;

DOI:10.1002/ejoc.201101146

Reference yield:

C18H34O12S → methyl 4-hydroxy-2,3,5-tri-O-methyl-α-D-arabinofuranosyl(1->4)-6-deoxy-2,3-di-O-methyl-6-(4-nitrophenylsulfonylamino)-α-D-glucopyranoside (1356387-55-7)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium azide / N,N-dimethyl-formamide / 80 °C / Inert atmosphere

2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 20 °C

3: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

4: [bis(acetoxy)iodo]benzene; iodine / dichloromethane / 3 h / 20 °C / Inert atmosphere; Irradiation

With sodium azide; [bis(acetoxy)iodo]benzene; palladium 10% on activated carbon; hydrogen; iodine; triethylamine; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201101146

Reference yield:

methyl 2,3,5-tri-O-methyl-α-D-arabinofuranosyl-(1->4)-6-azido-6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside (1357467-51-6) → methyl 4-hydroxy-2,3,5-tri-O-methyl-α-D-arabinofuranosyl(1->4)-6-deoxy-2,3-di-O-methyl-6-(4-nitrophenylsulfonylamino)-α-D-glucopyranoside (1356387-55-7)

Guidance literature:

Multi-step reaction with 3 steps

1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 20 °C

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

3: [bis(acetoxy)iodo]benzene; iodine / dichloromethane / 3 h / 20 °C / Inert atmosphere; Irradiation

With [bis(acetoxy)iodo]benzene; palladium 10% on activated carbon; hydrogen; iodine; triethylamine; In dichloromethane; ethyl acetate;

DOI:10.1002/ejoc.201101146

upstream raw materials:

methyl 2,3,5-tri-O-methyl-α-D-arabinofuranosyl(1->4)-6-deoxy-2,3-di-O-methyl-6-(4-nitrophenylsulfonylamino)-α-D-glucopyranoside

methyl 2,3,5-tri-O-methyl-α-D-arabinofuranosyl-(1→4)-6-O-(tert-butyldiphenylsilyl)-2,3-di-O-methyl-α-D-glucopyranoside

methyl 2,3,5-tri-O-methyl-α-D-arabinofuranosyl-(1->4)-2,3-di-O-methyl-α-D-glucopyranoside

methyl 2,3,5-tri-O-methyl-α-D-arabinofuranosyl-(1->4)-6-azido-6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside