2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-1,5-anhydro-2-deoxy-3,6-di-O-benzyl-D-arabino-hex-1-enitol

Base Information

• Chemical Name: 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-1,5-anhydro-2-deoxy-3,6-di-O-benzyl-D-arabino-hex-1-enitol
• CAS No.: 114117-12-3
• Molecular Formula: C₅₄H₅₆O₉
• Molecular Weight: 849.033
• Mol file: 114117-12-3.mol

Synonyms:2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-1,5-anhydro-2-deoxy-3,6-di-O-benzyl-D-arabino-hex-1-enitol

Chemical Property of 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-1,5-anhydro-2-deoxy-3,6-di-O-benzyl-D-arabino-hex-1-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-1,5-anhydro-2-deoxy-3,6-di-O-benzyl-D-arabino-hex-1-enitol

There total 4 articles about 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-1,5-anhydro-2-deoxy-3,6-di-O-benzyl-D-arabino-hex-1-enitol 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: 89.0%

hexa-O-acetyl-D-lactal (51450-24-9) + benzyl bromide (100-39-0) → 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-1,5-anhydro-2-deoxy-3,6-di-O-benzyl-D-arabino-hex-1-enitol (114117-12-3)

Guidance literature:

hexa-O-acetyl-D-lactal; With sodium methylate; In methanol; at 0 - 20 ℃; for 1h;

benzyl bromide; With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 5h;

DOI:10.1021/acs.joc.1c01318

Reference yield: 85.0%

benzyl bromide (100-39-0) + D-lactal (65207-55-8,5346-85-0) → 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-1,5-anhydro-2-deoxy-3,6-di-O-benzyl-D-arabino-hex-1-enitol (114117-12-3)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1039/b418247b

Reference yield: 65.0%

benzyl chloride (100-44-7) + D-lactal (65207-55-8,5346-85-0) → 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-1,5-anhydro-2-deoxy-3,6-di-O-benzyl-D-arabino-hex-1-enitol (114117-12-3)

Guidance literature:

With potassium hydroxide; In 1,4-dioxane; for 10h; Heating;

DOI:10.1016/0008-6215(87)80135-0

upstream raw materials:

benzyl chloride

D-lactal

benzyl bromide

hexa-O-acetyl-D-lactal

Downstream raw materials:

(E)-(2R,3R,4R)-1,4-Bis-benzyloxy-6-methoxy-3-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hex-5-en-2-ol

3,4,6-tri-O-benzyl-2,5-anhydro-D-allose dimethylacetal

Refernces

• 1、 Ruhela, Dipali,Chatterjee, Patrali,Vishwakarma, Ram A.. "1-Oxabicyclic β-lactams as new inhibitors of elongating MPT-a key enzyme responsible for assembly of cell-surface phosphoglycans of Leishmania parasite". . p. 1043 - 1048. Retrieved 2007/10/03.
• 2、 Kinzy, Willy,Schmidt, Richard R.. "APPLICATION OF THE TRICHLOROACETIMIDATE METHOD TO THE SYNTHESIS OF GLYCOPEPTIDES OF THE MUCIN TYPE CONTAINING A β-D-Galp-(1->3)-D-GalpNAc UNIT". . p. 265 - 276. Retrieved 2007/10/02.