O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

Base Information

• Chemical Name: O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
• CAS No.: 66080-60-2
• Molecular Formula: C₄₁H₅₁NO₁₁
• Molecular Weight: 733.856
• Mol file: 66080-60-2.mol

Synonyms:O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

Chemical Property of O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

There total 18 articles about O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 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: 92.0%

2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl diethyl phosphite + 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) → O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (66080-60-2) + 2-methyl-(3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-glucopyrano)-<2,1-d>-2-oxazoline (65372-02-3)

Guidance literature:

With bis(trifluoromethanesulfonyl)amide; In dichloromethane; at -78 ℃; for 1h; Inert atmosphere; Molecular sieve;

DOI:10.1021/acs.joc.5b00138

Reference yield: 87.0%

2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl acetate (65760-01-2) + 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) → O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (66080-60-2)

Guidance literature:

With iron(III) triflate - dimethylsulfoxide (1/6.2); In dichloromethane; at 45 ℃; for 16h; Reagent/catalyst; Sealed tube;

DOI:10.1021/acs.joc.6b02305

Reference yield: 80.0%

2-acetamido-1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranose (10583-63-8) + 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose → O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (66080-60-2)

Guidance literature:

With calcium sulfate; iron(III) chloride; tetramethylurea; In dichloromethane; Ambient temperature;

DOI:10.1016/0008-6215(85)85205-8

upstream raw materials:

2-acetamido-1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranose

allyl 2-acetamido-2-deoxy-β-D-glucopyranoside

2-propenyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

N-((3R,4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-2-hydroxy-tetrahydro-2H-pyran-3-yl)acetamide