Methyl 6-O-alpha-D-mannopyranosyl-alpha-D-Mannopyranoside

Base Information

• Chemical Name: Methyl 6-O-alpha-D-mannopyranosyl-alpha-D-Mannopyranoside
• CAS No.: 78962-39-7
• Molecular Formula: C₁₃H₂₄O₁₁
• Molecular Weight: 356.327
• DSSTox Substance ID: DTXSID001000164
• Nikkaji Number: J612.259K
• Wikidata: Q76296133
• Mol file: 78962-39-7.mol

Synonyms:M 6-O-MM;methyl 6-O-mannopyranosylmannopyranoside;methyl alpha-D-mannopyranosyl-(1-6)-alpha-D-mannopyranoside

Chemical Property of Methyl 6-O-alpha-D-mannopyranosyl-alpha-D-Mannopyranoside

Chemical Property:

• PSA: 178.53000
• LogP: -4.74310
• XLogP3: -4.2
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 5
• Exact Mass: 356.13186158
• Heavy Atom Count: 24
• Complexity: 396

Purity/Quality:

99% ^*data from raw suppliers

Methyl6-O-(α-D-Mannopyranosyl)-α-D-mannopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(C(C(O1)COC2C(C(C(C(O2)CO)O)O)O)O)O)O
• 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)CO)O)O)O)O)O)O
• Uses: Methyl 6-O-(α-D-Mannopyranosyl)-α-D-mannopyranoside is used in studies involving the antiviral agent cyanovirin-N and oligomannosides. It is also used in studies involving the glycomimetics of the C-glycosyl analog of the trisaccharide α-D-Man-(1 → 3)-[α-D-Man-(1 → 6)]-D-Man.

Technology Process of Methyl 6-O-alpha-D-mannopyranosyl-alpha-D-Mannopyranoside

There total 53 articles about Methyl 6-O-alpha-D-mannopyranosyl-alpha-D-Mannopyranoside 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: 98.0%

methyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-benzyl-2-O-picolinyl-β-D-glucopyranosyl)-α-D-glucopyranoside (873093-23-3) → methyl 6-O-(β-D-glucopyranosyl)-α-D-glucopyranoside (4159-55-1,13997-22-3,31083-50-8,52485-12-8,58462-70-7,76332-68-8,77790-33-1,78962-39-7,81131-45-5,100896-85-3,101144-26-7,101312-84-9,101398-94-1,105498-19-9,107911-44-4,111002-20-1,114817-78-6,117895-03-1,119617-59-3,127253-88-7,127253-89-8,136890-90-9,138809-03-7)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethanol; water; ethyl acetate; at 20 ℃; for 4h;

DOI:10.1002/anie.200502694

Reference yield: 97.0%

methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside (76679-49-7) → methyl 6-O-(β-D-glucopyranosyl)-α-D-glucopyranoside (4159-55-1,13997-22-3,31083-50-8,52485-12-8,58462-70-7,76332-68-8,77790-33-1,78962-39-7,81131-45-5,100896-85-3,101144-26-7,101312-84-9,101398-94-1,105498-19-9,107911-44-4,111002-20-1,114817-78-6,117895-03-1,119617-59-3,127253-88-7,127253-89-8,136890-90-9,138809-03-7)

Guidance literature:

With hydrogen; palladium;

DOI:10.1016/0040-4039(80)80236-X

Reference yield: 90.0%

2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate (149707-75-5) → methyl 6-O-(β-D-glucopyranosyl)-α-D-glucopyranoside (4159-55-1,13997-22-3,31083-50-8,52485-12-8,58462-70-7,76332-68-8,77790-33-1,78962-39-7,81131-45-5,100896-85-3,101144-26-7,101312-84-9,101398-94-1,105498-19-9,107911-44-4,111002-20-1,114817-78-6,117895-03-1,119617-59-3,127253-88-7,127253-89-8,136890-90-9,138809-03-7)

Guidance literature:

Multistep reaction;

DOI:10.1016/S0040-4039(01)01159-5

upstream raw materials:

methyl (2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)-β-(1→6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside

methyl 2,3,4-tri-O-benzoylglucopyranoside

2,3,4,6-tetra-O-benzoylglucosyl bromide

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