alpha-D-Xylopyranoside, methyl, 4-(4-methylbenzenesulfonate)

Base Information

• Chemical Name: alpha-D-Xylopyranoside, methyl, 4-(4-methylbenzenesulfonate)
• CAS No.: 14262-63-6
• Molecular Formula: C₁₃H₁₈O₇S
• Molecular Weight: 318.348
• DSSTox Substance ID: DTXSID801200085
• Nikkaji Number: J1.319.328B

Synonyms:DTXSID801200085;14262-63-6;alpha-D-Xylopyranoside, methyl, 4-(4-methylbenzenesulfonate)

Chemical Property of alpha-D-Xylopyranoside, methyl, 4-(4-methylbenzenesulfonate)

Chemical Property:

• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 318.07732408
• Heavy Atom Count: 21
• Complexity: 424

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC2COC(C(C2O)O)OC
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)O[C@@H]2CO[C@@H]([C@@H]([C@H]2O)O)OC

Technology Process of alpha-D-Xylopyranoside, methyl, 4-(4-methylbenzenesulfonate)

There total 4 articles about alpha-D-Xylopyranoside, methyl, 4-(4-methylbenzenesulfonate) 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: 9.0%

p-toluenesulfonyl chloride (98-59-9) + methyl-α-D-xylopyranoside (91-09-8) → methyl 2-O-p-toluenesulfonyl-α-D-xylopyranoside (14187-86-1) + methyl 4-O-p-toluenesulfonyl-α-D-xylopyranoside (14262-63-6) + methyl 3-O-p-tolylsulfonyl-α-D-xylopyranoside (84207-33-0) + methyl 2,4-di-O-p-tolylsulfonyl-α-D-xylopyranoside (84207-31-8)

Guidance literature:

In pyridine; Further byproducts given; one molar equivalent of p-toluenesulfonyl chloride;

DOI:10.1016/0008-6215(82)84018-4

Reference yield:

p-toluenesulfonyl chloride (98-59-9) + methyl-α-D-xylopyranoside (91-09-8) → methyl 2-O-p-toluenesulfonyl-α-D-xylopyranoside (14187-86-1) + methyl 4-O-p-toluenesulfonyl-α-D-xylopyranoside (14262-63-6) + methyl 2,4-di-O-p-tolylsulfonyl-α-D-xylopyranoside (84207-31-8)

Guidance literature:

With triethylamine; di(n-butyl)tin oxide; In 1,4-dioxane; at 20 ℃; Title compound not separated from byproducts.;

DOI:10.1021/ja016031r

Reference yield:

p-toluenesulfonyl chloride (98-59-9) + methyl-α-D-xylopyranoside (91-09-8) → methyl 2-O-p-toluenesulfonyl-α-D-xylopyranoside (14187-86-1) + methyl 4-O-p-toluenesulfonyl-α-D-xylopyranoside (14262-63-6)

Guidance literature:

With dmap; di(n-butyl)tin oxide; Yield given. Multistep reaction. Yields of byproduct given; 1.) MeOH, reflux, 3-10 h 2.) dioxane, room temp., 16 h;

DOI:10.1248/cpb.39.2883

upstream raw materials:

p-toluenesulfonyl chloride

methyl-α-D-xylopyranoside

Downstream raw materials:

methyl 2,3-di-O-benzoyl-4-O-p-toluenesulfonyl-α-D-xylopyranoside

methyl 4-deoxy-β-L-threo-pentopyranoside di-O-benzoate

methyl 2,3,4-tri-O-benzoyl-α-D-xylopyranoside

methyl 4-azido-2,3-di-O-benzoyl-4-deoxy-β-L-arabinopyranoside

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