Methyl 4-O-(methanesulfonyl)pentopyranoside

Base Information

• Chemical Name: Methyl 4-O-(methanesulfonyl)pentopyranoside
• CAS No.: 13143-94-7
• Molecular Formula: C₇H₁₄O₇S
• Molecular Weight: 242.25
• NSC Number: 92714
• DSSTox Substance ID: DTXSID50927197

Synonyms:13143-94-7;NSC92714;NCIOpen2_005810;DTXSID50927197;NSC-92714;Methyl 4-O-(methanesulfonyl)pentopyranoside

Chemical Property of Methyl 4-O-(methanesulfonyl)pentopyranoside

Chemical Property:

• Vapor Pressure: 9.9E-11mmHg at 25°C
• Refractive Index: 1.521
• Boiling Point: 468.1°Cat760mmHg
• Flash Point: 236.9°C
• Density: 1.49g/cm³
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 242.04602395
• Heavy Atom Count: 15
• Complexity: 295

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(C(CO1)OS(=O)(=O)C)O)O

Technology Process of Methyl 4-O-(methanesulfonyl)pentopyranoside

There total 3 articles about Methyl 4-O-(methanesulfonyl)pentopyranoside 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: 91.0%

methanesulfonyl chloride (124-63-0) + methyl β-L-arabinopyranoside (91-09-8,612-05-5,1825-00-9,2500-78-9,3867-83-2,3945-28-6,5328-63-2,6206-67-3,6207-01-8,6207-03-0,7404-24-2,14703-09-4,17289-61-1,18449-76-8,33509-64-7,36793-06-3,41897-31-8,41897-32-9,41897-33-0,41897-34-1,41897-37-4,41897-38-5,41897-39-6,53448-52-5,65137-86-2,89615-04-3,89615-05-4,131233-91-5) → Methyl-4-O-methylsulfonyl-β-L-arabinopyranosid (13143-94-7) + C7H14O7S (1452153-95-5)

Guidance literature:

With (2R,4S)-4-isopropyl-2-methoxy-3-((R)-2-methyl-1-(1-methyl-1H-imidazol-2-yl)propyl)oxazolidine; N,N-diisopropylethylamine hydrochloride; N-ethyl-N,N-diisopropylamine; at 4 ℃; for 4h; regioselective reaction;

DOI:10.1038/nchem.1726

Reference yield:

methanesulfonyl chloride (124-63-0) + methyl β-L-arabinopyranoside (91-09-8,612-05-5,1825-00-9,2500-78-9,3867-83-2,3945-28-6,5328-63-2,6206-67-3,6207-01-8,6207-03-0,7404-24-2,14703-09-4,17289-61-1,18449-76-8,33509-64-7,36793-06-3,41897-31-8,41897-32-9,41897-33-0,41897-34-1,41897-37-4,41897-38-5,41897-39-6,53448-52-5,65137-86-2,89615-04-3,89615-05-4,131233-91-5) → Methyl-4-O-methylsulfonyl-β-L-arabinopyranosid (13143-94-7) + C7H14O7S (1452153-95-5) + methyl-(O2-methanesulfonyl-β-L-arabinopyranoside) (1207271-88-2)

Guidance literature:

With 1-methyl-1H-imidazole; N,N-diisopropylethylamine hydrochloride; N-ethyl-N,N-diisopropylamine; at 4 ℃; for 4h; Overall yield = 27 %; regioselective reaction;

DOI:10.1038/nchem.1726

Reference yield:

→ Methyl-4-O-methylsulfonyl-β-L-arabinopyranosid (13143-94-7)

Guidance literature:

Methyl-2,3-di-O-benzoyl-4-O-methylsulfonyl-β-L-arabinopyranosid, methanol.Natriummethylat;

DOI:10.1021/jo01283a038

upstream raw materials:

methanesulfonyl chloride

methyl β-L-arabinopyranoside

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