Methyl-3,4,6-tri-O-methylmannoside

Base Information

• Chemical Name: Methyl-3,4,6-tri-O-methylmannoside
• CAS No.: 6150-07-8
• Molecular Formula: C₁₀H₂₀O₆
• Molecular Weight: 236.265
• DSSTox Substance ID: DTXSID101347640
• Nikkaji Number: J354.540G
• Wikidata: Q63409679
• Mol file: 6150-07-8.mol

Synonyms:METHYL-3,4,6-TRI-O-METHYLMANNOSIDE;6150-07-8;SCHEMBL7147863;DTXSID101347640;Methyl 3,4,6-tri-O-methylmannopyranoside;Q63409679

Chemical Property of Methyl-3,4,6-tri-O-methylmannoside

Chemical Property:

• XLogP3: -1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 236.12598835
• Heavy Atom Count: 16
• Complexity: 200

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COCC1C(C(C(C(O1)OC)O)OC)OC
• Isomeric SMILES: COC[C@@H]1[C@H]([C@@H]([C@@H]([C@H](O1)OC)O)OC)OC

Technology Process of Methyl-3,4,6-tri-O-methylmannoside

There total 39 articles about Methyl-3,4,6-tri-O-methylmannoside 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: 94.0%

methyl 2-O-benzyl-3,4,6-tri-O-methyl-β-D-glucopyranoside (128503-59-3) → methyl 3,4,6-tri-O-methyl-β-D-glucopyranoside (2348-00-7,3149-56-2,6150-07-8,13479-66-8,22323-61-1,22323-62-2,58462-87-6,64314-51-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 72h;

DOI:10.1002/ejoc.201101708

Reference yield: 41.0%

methanol (67-56-1) + (4S,5R,6R)-3-Bromo-4,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran-2-ol → methyl 3,4,6-tri-O-methyl-α-D-mannopyranoside (6150-07-8) + methyl 3,4,6-tri-O-methyl-β-D-glucopyranoside (2348-00-7,3149-56-2,6150-07-8,13479-66-8,22323-61-1,22323-62-2,58462-87-6,64314-51-8) + 2,5-anhydro-3-deoxy-4,6-di-O-methyl-aldehydo-D-erythro-hex-2-enitol

Guidance literature:

With caesium carbonate; 5 deg C, 4 h; rt, 15 h;

DOI:10.1016/S0008-6215(97)00054-2

Reference yield: 41.0%

methanol (67-56-1) + (4S,5R,6R)-3-Bromo-4,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran-2-ol → methyl 3,4,6-tri-O-methyl-α-D-mannopyranoside (6150-07-8) + methyl 3,4,6-tri-O-methyl-β-D-glucopyranoside (2348-00-7,3149-56-2,6150-07-8,13479-66-8,22323-61-1,22323-62-2,58462-87-6,64314-51-8) + 2,5-anhydro-3-deoxy-4,6-di-O-methyl-aldehydo-D-erythro-hex-2-enitol

Guidance literature:

With caesium carbonate; 5 deg C, 4 h; rt, 15 h;

DOI:10.1016/S0008-6215(97)00054-2

upstream raw materials:

methyl 2-O-benzyl-3,4,6-tri-O-methyl-β-D-glucopyranoside

methanol

sodium methylate

methyl-[O³,O⁴,O⁶-trimethyl-O²-(toluene-4-β-D-sulfonyl)-glucopyranoside]

Downstream raw materials:

methyl 2-O-acetyl-3,4,6-tri-O-methyl-α-D-mannopyranoside

Trimethyl-((2S,3S,4S,5R,6R)-2,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran-3-yloxy)-silane

3,4,6-tri-O-methyl-D-glucose

Refernces

• 1、 Matwiejuk, Martin,Thiem, Joachim. "Hydroxy group acidities of partially protected glycopyranosides". scheme or table. p. 2180 - 2187. Retrieved 2012/06/30.
• 2、 Fearnley, Stephen Philip,Lory, Pedro. "Intramolecular vinylsilane-oxocarbenium condensations: Concise assembly of cis-bicyclic ether arrays". . p. 3507 - 3510. Retrieved 2008/02/12.