methyl 4,6-O-benzylidene-2,3-di-O-methylhexopyranoside

Base Information

• Chemical Name: methyl 4,6-O-benzylidene-2,3-di-O-methylhexopyranoside
• CAS No.: 3051-89-6
• Molecular Formula: C₁₆H₂₂O₆
• Molecular Weight: 310.347
• NSC Number: 185315
• DSSTox Substance ID: DTXSID10952824
• Mol file: 3051-89-6.mol

Synonyms:NSC185315;methyl 4,6-O-benzylidene-2,3-di-O-methylhexopyranoside;DTXSID10952824;NSC-185315

Chemical Property of methyl 4,6-O-benzylidene-2,3-di-O-methylhexopyranoside

Chemical Property:

• Melting Point: 122-123 °C
• Boiling Point: 411.3°Cat760mmHg
• Flash Point: 168°C
• PSA: 55.38000
• Density: 1.2g/cm³
• LogP: 1.50190
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 310.14163842
• Heavy Atom Count: 22
• Complexity: 346

Purity/Quality:

99% ^*data from raw suppliers

Methyl 4,6-O-benzylidene-2,3-di-O-methyl-a-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C2C(COC(O2)C3=CC=CC=C3)OC(C1OC)OC

Technology Process of methyl 4,6-O-benzylidene-2,3-di-O-methylhexopyranoside

There total 49 articles about methyl 4,6-O-benzylidene-2,3-di-O-methylhexopyranoside 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: 98.2%

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside (3162-96-7) + methyl iodide (74-88-4) → methyl 4,6-O-benzylidene-2,3-di-O-methyl-α,D-glucopyranoside (3013-58-9,3051-89-6,4261-46-5,6748-99-8,13035-20-6,13502-46-0,22893-88-5,35311-32-1,53767-28-5,56586-53-9,56586-54-0,69744-11-2,94480-09-8,120200-48-8,120200-49-9,120200-50-2,120200-52-4)

Guidance literature:

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 1h;

methyl iodide; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃;

DOI:10.1016/j.bmcl.2017.06.008

Reference yield: 95.0%

methyl 4,6-O-benzylidene-α-D-glucopyranoside (3162-96-7) + methyl iodide (74-88-4) → methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-glucopyranoside (3013-58-9,3051-89-6,4261-46-5,6748-99-8,13035-20-6,13502-46-0,22893-88-5,35311-32-1,53767-28-5,56586-53-9,56586-54-0,69744-11-2,94480-09-8,120200-48-8,120200-49-9,120200-50-2,120200-52-4)

Guidance literature:

methyl 4,6-O-benzylidene-α-D-glucopyranoside; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 1.33333h;

methyl iodide; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 20.5h;

DOI:10.1021/ja402319m

Reference yield: 88.0%

methyl 4,6-O-benzylidene-α-D-glucopyranoside (3162-96-7) + methyl iodide (74-88-4) → methyl 4,6-O-benzylidene-2,3-di-O-methyl-α,D-glucopyranoside (3013-58-9,3051-89-6,4261-46-5,6748-99-8,13035-20-6,13502-46-0,22893-88-5,35311-32-1,53767-28-5,56586-53-9,56586-54-0,69744-11-2,94480-09-8,120200-48-8,120200-49-9,120200-50-2,120200-52-4)

Guidance literature:

methyl 4,6-O-benzylidene-α-D-glucopyranoside; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.333333h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; at 20 ℃; for 16h;

upstream raw materials:

Methyl 2,3-anhydro-4,6-O-(phenylmethylene)-β-D-allopyranoside

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside

benzylidene dichloride

methyl 2,3-di-O-methyl-α-D-glucopyranoside

Downstream raw materials:

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

methyl 4-O-benzyl-2,3-di-O-methyl-α-D-glucopyranoside

methyl 4-O-benzoyl-6-bromo-6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside

methyl 4-O-benzyl-6-bromo-6-deoxy-4-O-(methoxyethoxymethyl)-2,3-di-O-methyl-α-D-glucopyranoside

Refernces

• 1、 Wang, Dong-dong,Li, Xiao-san,Bao, Yu-zhou,Liu, Jie,Zhang, Xiao-kun,Yao, Xin-sheng,Sun, Xue-Long,Tang, Jin-Shan. "Synthesis of MeON-neoglycosides of digoxigenin with 6-deoxy- and 2,6-dideoxy-D-glucose derivatives and their anticancer activity". supporting information. p. 3359 - 3364. Retrieved 2017/07/07.
• 2、 Banerjee, Amit,Senthilkumar, Soundararasu,Baskaran, Sundarababu. "Benzylidene Acetal Protecting Group as Carboxylic Acid Surrogate: Synthesis of Functionalized Uronic Acids and Sugar Amino Acids". supporting information. p. 902 - 906. Retrieved 2016/01/16.