Methyl 2,3,4-tris-O-(phenylmethyl)-6-O-[2,3,4,6-tetrakis-O-(phenylmethyl)-alpha-D-glucopyranosyl]-beta-D-glucopyranoside

Base Information

• Chemical Name: Methyl 2,3,4-tris-O-(phenylmethyl)-6-O-[2,3,4,6-tetrakis-O-(phenylmethyl)-alpha-D-glucopyranosyl]-beta-D-glucopyranoside
• CAS No.: 108739-68-0
• Molecular Formula: C₆₂H₆₆O₁₁
• Molecular Weight: 987.199
• DSSTox Substance ID: DTXSID801107182
• Nikkaji Number: J734.830D
• Mol file: 108739-68-0.mol

Synonyms:DTXSID801107182;108739-68-0;Methyl 2,3,4-tris-O-(phenylmethyl)-6-O-[2,3,4,6-tetrakis-O-(phenylmethyl)-alpha-D-glucopyranosyl]-beta-D-glucopyranoside

Chemical Property of Methyl 2,3,4-tris-O-(phenylmethyl)-6-O-[2,3,4,6-tetrakis-O-(phenylmethyl)-alpha-D-glucopyranosyl]-beta-D-glucopyranoside

Chemical Property:

• XLogP3: 9.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 26
• Exact Mass: 986.46051292
• Heavy Atom Count: 73
• Complexity: 1430

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1C(C(C(C(O1)COC2C(C(C(C(O2)COCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5)OCC6=CC=CC=C6)OCC7=CC=CC=C7)OCC8=CC=CC=C8)OCC9=CC=CC=C9
• Isomeric SMILES: CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)COCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5)OCC6=CC=CC=C6)OCC7=CC=CC=C7)OCC8=CC=CC=C8)OCC9=CC=CC=C9

Technology Process of Methyl 2,3,4-tris-O-(phenylmethyl)-6-O-[2,3,4,6-tetrakis-O-(phenylmethyl)-alpha-D-glucopyranosyl]-beta-D-glucopyranoside

There total 533 articles about Methyl 2,3,4-tris-O-(phenylmethyl)-6-O-[2,3,4,6-tetrakis-O-(phenylmethyl)-alpha-D-glucopyranosyl]-beta-D-glucopyranoside 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: 99.0%

methyl 2,3,4-tri-O-benzyl-6-O-(trimethylsilyl)-α-D-glucopyranoside (78687-40-8) + 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate (339276-14-1) → methyl O-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyll-α-D-glucopyranoside (56632-57-6,61474-61-1,108739-68-0,108739-69-1,117894-96-9,117894-97-0,123806-49-5,123806-50-8,129832-16-2,130794-95-5,139403-38-6,144069-05-6,144069-06-7,151379-73-6,151379-74-7,55094-26-3)

Guidance literature:

With trimethylsilyl iodide; Triphenylphosphine oxide; In dichloromethane; at 18 ℃; for 48h; stereoselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.1c02947

Reference yield: 97.0%

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) + C59H53NO10 → methyl O-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyll-α-D-glucopyranoside (56632-57-6,61474-61-1,108739-68-0,108739-69-1,117894-96-9,117894-97-0,123806-49-5,123806-50-8,129832-16-2,130794-95-5,139403-38-6,144069-05-6,144069-06-7,151379-73-6,151379-74-7,55094-26-3) + C25H19NO5

Guidance literature:

With calcium sulfate; [Ag(MeCN)₂][B{C₆H₃(CF₃)₂-3,5}₄]; α,α,α-trifluorotoluene; chloro[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold(I); In cyclohexane; at -15 ℃; for 15h; stereoselective reaction;

DOI:10.1021/jacs.1c04584

Reference yield: 96.0%

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) + 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (74808-09-6) → methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1-6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside (55094-26-3,61474-61-1,108739-68-0,108739-69-1,117894-96-9,117894-97-0,123806-49-5,123806-50-8,129832-16-2,130794-95-5,139403-38-6,144069-05-6,144069-06-7,151379-73-6,151379-74-7,56632-57-6)

Guidance literature:

With diphenylboron fluoride; In dichloromethane; at -78 ℃; for 0.166667h; optical yield given as %de; stereoselective reaction;

DOI:10.1021/ol201231v

upstream raw materials:

2-benzothiazolyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide

1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose

Downstream raw materials:

methyl O-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyll-α-D-glucopyranoside