methyl dimethylthexylsilyl 4-O-(2-azido-3,4-di-O-benzyl-2-deoxy-[6-O-(4-methoxybenzyl)]-α-D-glucopyranosyl)-3-O-benzyl-2-O-benzoyl-β-L-idopyranosyluronate

Base Information

• Chemical Name: methyl dimethylthexylsilyl 4-O-(2-azido-3,4-di-O-benzyl-2-deoxy-[6-O-(4-methoxybenzyl)]-α-D-glucopyranosyl)-3-O-benzyl-2-O-benzoyl-β-L-idopyranosyluronate
• CAS No.: 616876-52-9
• Molecular Formula: C₅₇H₆₉N₃O₁₃Si
• Molecular Weight: 1032.27
• Mol file: 616876-52-9.mol

Synonyms:methyl dimethylthexylsilyl 4-O-(2-azido-3,4-di-O-benzyl-2-deoxy-[6-O-(4-methoxybenzyl)]-α-D-glucopyranosyl)-3-O-benzyl-2-O-benzoyl-β-L-idopyranosyluronate

Chemical Property of methyl dimethylthexylsilyl 4-O-(2-azido-3,4-di-O-benzyl-2-deoxy-[6-O-(4-methoxybenzyl)]-α-D-glucopyranosyl)-3-O-benzyl-2-O-benzoyl-β-L-idopyranosyluronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl dimethylthexylsilyl 4-O-(2-azido-3,4-di-O-benzyl-2-deoxy-[6-O-(4-methoxybenzyl)]-α-D-glucopyranosyl)-3-O-benzyl-2-O-benzoyl-β-L-idopyranosyluronate

There total 5 articles about methyl dimethylthexylsilyl 4-O-(2-azido-3,4-di-O-benzyl-2-deoxy-[6-O-(4-methoxybenzyl)]-α-D-glucopyranosyl)-3-O-benzyl-2-O-benzoyl-β-L-idopyranosyluronate 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: 96.0%

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) + methyl (dimethylthexylsilyl 4-O-(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-2-O-benzoyl-β-L-idopyranosyl)uronate (635288-14-1) → methyl dimethylthexylsilyl 4-O-(2-azido-3,4-di-O-benzyl-2-deoxy-[6-O-(4-methoxybenzyl)]-α-D-glucopyranosyl)-3-O-benzyl-2-O-benzoyl-β-L-idopyranosyluronate (616876-52-9)

Guidance literature:

With boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane; at -20 ℃; for 0.166667h;

DOI:10.1039/b303115b

Reference yield: 51.0%

benzoyl chloride (98-88-4) + methyl (dimethylthexylsilyl 3-O-benzyl-β-L-idopyranoside)uronate (243982-79-8) + 2,2,2-Trichloro-acetimidic acid (3R,4R,5S,6R)-3-azido-4,5-bis-benzyloxy-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl ester → methyl dimethylthexylsilyl 4-O-(2-azido-3,4-di-O-benzyl-2-deoxy-[6-O-(4-methoxybenzyl)]-α-D-glucopyranosyl)-3-O-benzyl-2-O-benzoyl-β-L-idopyranosyluronate (616876-52-9)

Guidance literature:

methyl (dimethylthexylsilyl 3-O-benzyl-β-L-idopyranoside)uronate; 2,2,2-Trichloro-acetimidic acid (3R,4R,5S,6R)-3-azido-4,5-bis-benzyloxy-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl ester; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane;

benzoyl chloride;

DOI:10.1002/ejoc.200300210

Reference yield:

benzoyl chloride (98-88-4) → methyl dimethylthexylsilyl 4-O-(2-azido-3,4-di-O-benzyl-2-deoxy-[6-O-(4-methoxybenzyl)]-α-D-glucopyranosyl)-3-O-benzyl-2-O-benzoyl-β-L-idopyranosyluronate (616876-52-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / DMAP / pyridine / 18 h / 20 °C

2: 81 percent / BH₃*NMe₂; BF₃*Et₂O / CH₂Cl₂ / 0.5 h / -15 °C

3: 96 percent / BF₃*OEt₂ / CH₂Cl₂; tetrahydrofuran / 0.17 h / -20 °C

With dmap; dimethylamine borane; boron trifluoride diethyl etherate; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1039/b303115b

upstream raw materials:

O-(4-methoxybenzyl)-trichloroacetimidate

methyl (dimethylthexylsilyl 4-O-(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-2-O-benzoyl-β-L-idopyranosyl)uronate

benzoyl chloride

methyl (dimethylthexylsilyl 3-O-benzyl-β-L-idopyranoside)uronate