Methyl 2-C-methyl-4,6-O-(phenylmethylene)-alpha-D-glucopyranoside

Base Information

• Chemical Name: Methyl 2-C-methyl-4,6-O-(phenylmethylene)-alpha-D-glucopyranoside
• CAS No.: 60574-71-2
• Molecular Formula: C₁₅H₂₀O₆
• Molecular Weight: 296.32
• DSSTox Substance ID: DTXSID101183018

Synonyms:DTXSID101183018;Methyl 2-C-methyl-4,6-O-(phenylmethylene)-alpha-D-glucopyranoside;60574-71-2

Chemical Property of Methyl 2-C-methyl-4,6-O-(phenylmethylene)-alpha-D-glucopyranoside

Chemical Property:

• XLogP3: 0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 296.12598835
• Heavy Atom Count: 21
• Complexity: 358

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(C(C2C(COC(O2)C3=CC=CC=C3)OC1OC)O)O
• Isomeric SMILES: C[C@]1([C@H]([C@H]2[C@@H](COC(O2)C3=CC=CC=C3)O[C@@H]1OC)O)O

Technology Process of Methyl 2-C-methyl-4,6-O-(phenylmethylene)-alpha-D-glucopyranoside

There total 3 articles about Methyl 2-C-methyl-4,6-O-(phenylmethylene)-alpha-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: 34.0%

methyl 3-O-benzoyl-4,6-O-benzylidene-α-D-arabino-hexopyranosid-2-ulose (38993-01-0) + methyl iodide (74-88-4) → methyl 4,6-O-benzylidene-2-C-methyl-α-D-glucopyranoside (60574-71-2) + (4aR,6S,7S,8S,8aS)-6-Methoxy-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (60574-72-3)

Guidance literature:

With magnesium; In diethyl ether; benzene; for 1.5h; Heating;

DOI:10.1016/0008-6215(84)85203-9

Reference yield: 33.0%

methyl 3-O-benzoyl-4,6-O-benzylidene-α-D-arabino-hexopyranosid-2-ulose (38993-01-0) + methyl iodide (74-88-4) → methyl 3-O-benzoyl-4,6-benzylidene-2-C-methyl-α-D-glucopyranoside (60574-69-8) + methyl 4,6-O-benzylidene-2-C-methyl-α-D-glucopyranoside (60574-71-2)

Guidance literature:

With magnesium; In diethyl ether; Product distribution; furhter solvent, different times and temperatures;

DOI:10.1016/0008-6215(84)85203-9

Reference yield:

→ methyl 4,6-O-benzylidene-2-C-methyl-α-D-glucopyranoside (60574-71-2)

Guidance literature:

Alkohol 2, BaO /CH3OH, Abspaltung der Benzoylgruppe;

DOI:10.1246/bcsj.49.1686

upstream raw materials:

methyl 3-O-benzoyl-4,6-O-benzylidene-α-D-arabino-hexopyranosid-2-ulose

methyl iodide

Downstream raw materials:

methyl 4,6-O-benzylidene-2-C-methyl-α-D-ribo-hexopyranosid-3-ulose

methyl 4,6-O-benzylidene-2-C-methyl-2-O-(methylthio)methyl-α-D-ribo-hexopyranosid-3-ulose

methyl 4,6-O-benzylidene-2-C-methyl-3-O-tosyl-α-D-glucopyranosdie

methyl 2,3-anhydro-4,6-O-benzylidene-2-C-methyl-α-D-mannopyranoside

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