octyl 2,4-di-O-benzyl-3-O-tert-butyldimethylsilyl-α-L-fucopyranosyl-(1->3)-2,4-di-O-benzyl-α-L-fucopyranosyl-(1->3)-2,4-di-O-benzyl-β-L-fucopyranoside

Base Information

• Chemical Name: octyl 2,4-di-O-benzyl-3-O-tert-butyldimethylsilyl-α-L-fucopyranosyl-(1->3)-2,4-di-O-benzyl-α-L-fucopyranosyl-(1->3)-2,4-di-O-benzyl-β-L-fucopyranoside
• CAS No.: 685110-01-4
• Molecular Formula: C₇₄H₉₈O₁₃Si
• Molecular Weight: 1223.67
• Mol file: 685110-01-4.mol

Synonyms:octyl 2,4-di-O-benzyl-3-O-tert-butyldimethylsilyl-α-L-fucopyranosyl-(1->3)-2,4-di-O-benzyl-α-L-fucopyranosyl-(1->3)-2,4-di-O-benzyl-β-L-fucopyranoside

Chemical Property of octyl 2,4-di-O-benzyl-3-O-tert-butyldimethylsilyl-α-L-fucopyranosyl-(1->3)-2,4-di-O-benzyl-α-L-fucopyranosyl-(1->3)-2,4-di-O-benzyl-β-L-fucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of octyl 2,4-di-O-benzyl-3-O-tert-butyldimethylsilyl-α-L-fucopyranosyl-(1->3)-2,4-di-O-benzyl-α-L-fucopyranosyl-(1->3)-2,4-di-O-benzyl-β-L-fucopyranoside

There total 7 articles about octyl 2,4-di-O-benzyl-3-O-tert-butyldimethylsilyl-α-L-fucopyranosyl-(1->3)-2,4-di-O-benzyl-α-L-fucopyranosyl-(1->3)-2,4-di-O-benzyl-β-L-fucopyranoside 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: 80.0%

ethyl 2,4-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-L-fucopyranoside (685109-95-9) + octyl 2,4-di-O-benzyl-α-L-fucopyranosyl-(1->3)-2,4-di-O-benzyl-β-L-fucopyranoside (685110-00-3) → octyl 2,4-di-O-benzyl-3-O-tert-butyldimethylsilyl-α-L-fucopyranosyl-(1->3)-2,4-di-O-benzyl-α-L-fucopyranosyl-(1->3)-2,4-di-O-benzyl-β-L-fucopyranoside (685110-01-4)

Guidance literature:

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 ℃; for 1h;

DOI:10.1016/j.carres.2003.12.014

Reference yield:

benzyl bromide (100-39-0) → octyl 2,4-di-O-benzyl-3-O-tert-butyldimethylsilyl-α-L-fucopyranosyl-(1->3)-2,4-di-O-benzyl-α-L-fucopyranosyl-(1->3)-2,4-di-O-benzyl-β-L-fucopyranoside (685110-01-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 97 percent / NaH / dimethylformamide / 2.5 h / 0 - 20 °C

2: 97 percent / N-iodosuccinimide; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 1 h / -20 °C

3: 89 percent / tetrabutylammonium fluoride monohydrate / tetrahydrofuran / 2 h / 20 °C

4: 89 percent / N-iodosuccinimide; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 1 h / -20 °C

5: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C

6: 80 percent / N-iodosuccinimide; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 1 h / -20 °C

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2003.12.014

Reference yield:

ethyl 1-thio-α-L-fucopyranoside (132799-10-1) → octyl 2,4-di-O-benzyl-3-O-tert-butyldimethylsilyl-α-L-fucopyranosyl-(1->3)-2,4-di-O-benzyl-α-L-fucopyranosyl-(1->3)-2,4-di-O-benzyl-β-L-fucopyranoside (685110-01-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 92 percent / imidazole / dimethylformamide / 2.5 h / 0 - 20 °C

2: 97 percent / NaH / dimethylformamide / 2.5 h / 0 - 20 °C

3: 97 percent / N-iodosuccinimide; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 1 h / -20 °C

4: 89 percent / tetrabutylammonium fluoride monohydrate / tetrahydrofuran / 2 h / 20 °C

5: 89 percent / N-iodosuccinimide; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 1 h / -20 °C

6: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C

7: 80 percent / N-iodosuccinimide; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 1 h / -20 °C

With 1H-imidazole; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2003.12.014

upstream raw materials:

ethyl 2,4-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-L-fucopyranoside

octyl 2,4-di-O-benzyl-α-L-fucopyranosyl-(1->3)-2,4-di-O-benzyl-β-L-fucopyranoside

benzyl bromide

ethyl 1-thio-α-L-fucopyranoside

Downstream raw materials:

octyl 2,4-di-O-benzyl-α-L-fucopyranosyl-(1->3)-2,4-di-O-benzyl-α-L-fucopyranosyl-(1->3)-2,4-di-O-benzyl-β-L-fucopyranoside