6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosyluronate

Base Information

• Chemical Name: 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosyluronate
• CAS No.: 444118-47-2
• Molecular Formula: C₃₈H₅₃N₃O₁₂Si
• Molecular Weight: 771.937
• Mol file: 444118-47-2.mol

Synonyms:6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosyluronate

Chemical Property of 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosyluronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosyluronate

There total 13 articles about 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosyluronate 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: 86.0%

methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosiduronate (444118-41-6) + 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α/β-D-glucopyranosyl trichloroacetimidate → 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosyluronate (444118-47-2)

Guidance literature:

With 4 A molecular sieve; t-butyldimethylsiyl triflate; In dichloromethane; at -78 - 20 ℃; for 2.5h;

DOI:10.1002/1521-3773(20020617)41:12<2128::AID-ANIE2128>3.0.CO;2-V

Reference yield: 80.0%

methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosiduronate (444118-41-6) + 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α/β-D-glucopyranosyl fluoride → 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosyluronate (444118-47-2)

Guidance literature:

With 4 A molecular sieve; silver perchlorate; tin(ll) chloride; In diethyl ether; at 0 - 20 ℃;

DOI:10.1002/1521-3773(20020617)41:12<2128::AID-ANIE2128>3.0.CO;2-V

Reference yield:

methyl 3-O-benzyl-D-glucopyranosyluronate → 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosyluronate (444118-47-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 48 percent / (1S)-(+)-camphorsulfonic acid / dimethylformamide / 0 - 20 °C

2: 80 percent / molecular sieves 4 Angstroem; AgClO₄; SnCl₂ / diethyl ether / 23.5 h / 0 - 12 °C

With 4 A molecular sieve; silver perchlorate; (+)-10-camphorsulfonic acid; tin(ll) chloride; In diethyl ether; N,N-dimethyl-formamide;

DOI:10.1002/chem.200390009

upstream raw materials:

methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosiduronate

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

benzyl bromide

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose

Downstream raw materials:

pent-4-enyl (methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosyluronate)-(1->4)-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate

pent-4-enyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate

6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 2-O-levulinoyl-3-O-benzyl-α-D-glucopyranosyluronate trichloroacetimidate

tert-butyldimethylsilyl (6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate