(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1->4)-1-O-methyl-2,3,6-tri-O-benzyl-α-D-glucopyranose

Base Information

• Chemical Name: (2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1->4)-1-O-methyl-2,3,6-tri-O-benzyl-α-D-glucopyranose
• CAS No.: 1037510-13-6
• Molecular Formula: C₅₅H₅₈O₁₁
• Molecular Weight: 895.059

Synonyms:(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1->4)-1-O-methyl-2,3,6-tri-O-benzyl-α-D-glucopyranose

Chemical Property of (2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1->4)-1-O-methyl-2,3,6-tri-O-benzyl-α-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1->4)-1-O-methyl-2,3,6-tri-O-benzyl-α-D-glucopyranose

There total 4 articles about (2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1->4)-1-O-methyl-2,3,6-tri-O-benzyl-α-D-glucopyranose 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: 90.0%

2,3-di-O-benzyl-4,6-O-benzylidene-α/β-D-mannopyranose (20770-84-7,113566-69-1,113566-70-4) + methyl 2,3,6-tri-O-benzyl-α-D-mannopyranoside (19488-48-3,19488-49-4,51842-16-1,55697-49-9,115414-37-4,95475-33-5) → (2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1->4)-1-O-methyl-2,3,6-tri-O-benzyl-α-D-glucopyranose (1037510-13-6)

Guidance literature:

2,3-di-O-benzyl-4,6-O-benzylidene-α/β-D-mannopyranose; With phthalic anhydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 0.25h; Molecular sieve; Inert atmosphere;

With trifluoromethylsulfonic anhydride; di-tert-butylmethylpyridine; In dichloromethane; at -78 ℃; for 0.25h; Inert atmosphere;

methyl 2,3,6-tri-O-benzyl-α-D-mannopyranoside; In dichloromethane; at -78 - 0 ℃; stereoselective reaction; Inert atmosphere;

DOI:10.1021/ja710935z

Reference yield: 85.0%

2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl pent-4-enoate (920976-12-1) + methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) → (2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1->4)-1-O-methyl-2,3,6-tri-O-benzyl-α-D-glucopyranose (1037510-13-6)

Guidance literature:

2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl pent-4-enoate; With 4 A molecular sieve; Phenylselenyl bromide; 2,4,6-tri-tert-butylpyrimidine; silver trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 0.25h;

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside; In dichloromethane; for 1.66667h; cooling;

DOI:10.1002/anie.200602642

Reference yield: 83.0%

methyl 2,3,6-tri-O-benzyl-α-D-mannopyranoside (19488-48-3,19488-49-4,51842-16-1,55697-49-9,115414-37-4,95475-33-5) + phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (159407-17-7) → (2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1->4)-1-O-methyl-2,3,6-tri-O-benzyl-α-D-glucopyranose (1037510-13-6)

Guidance literature:

phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside; With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -60 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

methyl 2,3,6-tri-O-benzyl-α-D-mannopyranoside; In dichloromethane; at -78 - 0 ℃; stereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1016/j.tet.2010.02.052

upstream raw materials:

2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl pent-4-enoate

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-α-D-mannopyranoside

2,3-di-O-benzyl-4,6-O-benzylidene-α/β-D-mannopyranose

Downstream raw materials:

methyl (2,3-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-mannopyranoside

methyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-mannopyranoside

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