1,2-[2',6'-di-O-benzyl-3-O-(3'',4'',5'',7''-tetra-O-methyl-1''-deoxy-1''-ethylsulfonato-α-D-gluco-hept-2''-ulopyranosyl)-β-D-galactopyranosyloxy]-(2,3,4-tri-O-benzyl-α-L-fucopyranosyloxy)ethane

Base Information

• Chemical Name: 1,2-[2',6'-di-O-benzyl-3-O-(3'',4'',5'',7''-tetra-O-methyl-1''-deoxy-1''-ethylsulfonato-α-D-gluco-hept-2''-ulopyranosyl)-β-D-galactopyranosyloxy]-(2,3,4-tri-O-benzyl-α-L-fucopyranosyloxy)ethane
• CAS No.: 286860-94-4
• Molecular Formula: C₆₂H₈₀O₁₉S
• Molecular Weight: 1161.37
• Mol file: 286860-94-4.mol

Synonyms:1,2-[2',6'-di-O-benzyl-3-O-(3'',4'',5'',7''-tetra-O-methyl-1''-deoxy-1''-ethylsulfonato-α-D-gluco-hept-2''-ulopyranosyl)-β-D-galactopyranosyloxy]-(2,3,4-tri-O-benzyl-α-L-fucopyranosyloxy)ethane

Chemical Property of 1,2-[2',6'-di-O-benzyl-3-O-(3'',4'',5'',7''-tetra-O-methyl-1''-deoxy-1''-ethylsulfonato-α-D-gluco-hept-2''-ulopyranosyl)-β-D-galactopyranosyloxy]-(2,3,4-tri-O-benzyl-α-L-fucopyranosyloxy)ethane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-[2',6'-di-O-benzyl-3-O-(3'',4'',5'',7''-tetra-O-methyl-1''-deoxy-1''-ethylsulfonato-α-D-gluco-hept-2''-ulopyranosyl)-β-D-galactopyranosyloxy]-(2,3,4-tri-O-benzyl-α-L-fucopyranosyloxy)ethane

There total 4 articles about 1,2-[2',6'-di-O-benzyl-3-O-(3'',4'',5'',7''-tetra-O-methyl-1''-deoxy-1''-ethylsulfonato-α-D-gluco-hept-2''-ulopyranosyl)-β-D-galactopyranosyloxy]-(2,3,4-tri-O-benzyl-α-L-fucopyranosyloxy)ethane 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: 55.0%

ethyl 1-deoxy-1-ethylsulfonato-3,4,5,7-tetra-O-methyl-2-thio-α-D-gluco-hept-2-ulopyranoside + 1,2-(2',6'-di-O-benzyl-β-D-galactopyranosyloxy)-(2,3,4-tri-O-benzyl-α-L-fucopyranosyloxy)ethane (286860-92-2) → 2,6-anhydro-3,4,5,7-tetra-O-methyl-1-ethylsulfonato-D-gluco-hept-1-enitol + 1,2-[2',6'-di-O-benzyl-3-O-(3'',4'',5'',7''-tetra-O-methyl-1''-deoxy-1''-ethylsulfonato-α-D-gluco-hept-2''-ulopyranosyl)-β-D-galactopyranosyloxy]-(2,3,4-tri-O-benzyl-α-L-fucopyranosyloxy)ethane (286860-94-4)

Guidance literature:

With 4 A molecular sieve; methyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1016/S0957-4166(99)00564-9

Reference yield:

2,3,4,6-tetra-O-methyl-D-glucopyranose (1139-97-5,1139-98-6,1851-12-3,3353-52-4,6163-35-5,14184-49-7,19146-17-9,22248-57-3,34361-56-3,34361-57-4,57793-53-0,7506-68-5) → 1,2-[2',6'-di-O-benzyl-3-O-(3'',4'',5'',7''-tetra-O-methyl-1''-deoxy-1''-ethylsulfonato-α-D-gluco-hept-2''-ulopyranosyl)-β-D-galactopyranosyloxy]-(2,3,4-tri-O-benzyl-α-L-fucopyranosyloxy)ethane (286860-94-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 85 percent / Dess-Martin's periodinane / CH₂Cl₂ / 0.5 h / 20 °C

2.1: LDA / tetrahydrofuran; hexane / 0.25 h / -60 °C

2.2: 50 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.1: 94 percent / BF₃*Et₂O / CH₂Cl₂ / 6 h / 20 °C

4.1: 55 percent / 4 Angstroem sieves; methyl trifluoromethanesulfonate / CH₂Cl₂ / 48 h / 20 °C

With 4 A molecular sieve; boron trifluoride diethyl etherate; Dess-Martin periodane; methyl trifluoromethanesulfonate; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; 1.1: Oxidation / 2.1: Metallation / 2.2: Addition / 3.1: Thioglycosidation / 4.1: Glycosylation;

DOI:10.1016/S0957-4166(99)00564-9

Reference yield:

1-deoxy-1-ethylsulfonato-3,4,5,7-tetra-O-methyl-α-D-gluco-hept-2-ulose (286860-81-9) → 1,2-[2',6'-di-O-benzyl-3-O-(3'',4'',5'',7''-tetra-O-methyl-1''-deoxy-1''-ethylsulfonato-α-D-gluco-hept-2''-ulopyranosyl)-β-D-galactopyranosyloxy]-(2,3,4-tri-O-benzyl-α-L-fucopyranosyloxy)ethane (286860-94-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / BF₃*Et₂O / CH₂Cl₂ / 6 h / 20 °C

2: 55 percent / 4 Angstroem sieves; methyl trifluoromethanesulfonate / CH₂Cl₂ / 48 h / 20 °C

With 4 A molecular sieve; boron trifluoride diethyl etherate; methyl trifluoromethanesulfonate; In dichloromethane; 1: Thioglycosidation / 2: Glycosylation;

DOI:10.1016/S0957-4166(99)00564-9

upstream raw materials:

1,2-(2',6'-di-O-benzyl-β-D-galactopyranosyloxy)-(2,3,4-tri-O-benzyl-α-L-fucopyranosyloxy)ethane

2,3,4,6-tetra-O-methyl-D-glucopyranose

1-deoxy-1-ethylsulfonato-3,4,5,7-tetra-O-methyl-α-D-gluco-hept-2-ulose

2,3,4,6-tetra-O-methyl-D-glucono-1,5-lactone