Methyl 4,6-o-benzylidene-2,3-bis-o-(methylsulfonyl)hexopyranoside

Base Information

• Chemical Name: Methyl 4,6-o-benzylidene-2,3-bis-o-(methylsulfonyl)hexopyranoside
• CAS No.: 6619-12-1
• Molecular Formula: C₁₆H₂₂O₁₀S₂
• Molecular Weight: 438.477
• NSC Number: 89883
• DSSTox Substance ID: DTXSID60293496

Synonyms:6619-12-1;NSC89883;DTXSID60293496;methyl 4,6-o-benzylidene-2,3-bis-o-(methylsulfonyl)hexopyranoside;NSC-89883

Chemical Property of Methyl 4,6-o-benzylidene-2,3-bis-o-(methylsulfonyl)hexopyranoside

Chemical Property:

• Vapor Pressure: 2.04E-16mmHg at 25°C
• Refractive Index: 1.569
• Boiling Point: 657.2°Cat760mmHg
• Flash Point: 351.2°C
• Density: 1.48g/cm³
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 6
• Exact Mass: 438.06543924
• Heavy Atom Count: 28
• Complexity: 720

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(C2C(O1)COC(O2)C3=CC=CC=C3)OS(=O)(=O)C)OS(=O)(=O)C

Technology Process of Methyl 4,6-o-benzylidene-2,3-bis-o-(methylsulfonyl)hexopyranoside

There total 3 articles about Methyl 4,6-o-benzylidene-2,3-bis-o-(methylsulfonyl)hexopyranoside 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: 81.0%

methyl 4,6-O-benzylidene-α-D-allopyranoside (79549-74-9) + methanesulfonyl chloride (124-63-0) → methyl 4,6-O-benzylidene-2,3-O-p-methanesulfonyl-α-D-gluco-pyranoside (6619-12-1,18929-72-1,23819-27-4,23819-32-1,24017-81-0,26532-07-0,26540-58-9,65530-21-4,65530-23-6)

Guidance literature:

In pyridine; for 24h; Ambient temperature;

DOI:10.1139/v82-050

Reference yield: 67.0%

benzaldehyde dimethyl acetal (1125-88-8) + methanesulfonyl chloride (124-63-0) + methyl beta-D-galactopyranoside (1824-94-8) → Methyl-4,6-benzyliden-2,3-di-O-mesyl-β-D-galactosid (6619-12-1,18929-72-1,23819-27-4,23819-32-1,24017-81-0,26532-07-0,26540-58-9,65530-21-4,65530-23-6)

Guidance literature:

benzaldehyde dimethyl acetal; methyl beta-D-galactopyranoside; With camphor-10-sulfonic acid; In N,N-dimethyl-formamide;

methanesulfonyl chloride; With pyridine;

DOI:10.1021/jo300764k

Reference yield:

→ Methyl-4,6-benzyliden-2,3-di-O-mesyl-β-D-galactosid (6619-12-1,18929-72-1,23819-27-4,23819-32-1,24017-81-0,26532-07-0,26540-58-9,65530-21-4,65530-23-6)

Guidance literature:

Methyl-4,6-O-benzyliden-β-D-galactosid, CH3-SO2-Cl;

DOI:10.1016/S0040-4020(01)93029-7

upstream raw materials:

benzaldehyde dimethyl acetal

methanesulfonyl chloride

methyl beta-D-galactopyranoside

methyl 4,6-O-benzylidene-α-D-allopyranoside

Downstream raw materials:

Benzoic acid (2S,3R,4S,5R,6S)-2-bromomethyl-4,5-bis-methanesulfonyloxy-6-methoxy-tetrahydro-pyran-3-yl ester

methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside

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