Glucopyranoside, methyl, 2,3-dibenzoate 4-p-toluenesulfonate, alpha-D-

Base Information

• Chemical Name: Glucopyranoside, methyl, 2,3-dibenzoate 4-p-toluenesulfonate, alpha-D-
• CAS No.: 19488-44-9
• Molecular Formula: C₂₈H₂₈O₁₀S
• Molecular Weight: 556.59
• DSSTox Substance ID: DTXSID601165467
• Mol file: 19488-44-9.mol

Synonyms:DTXSID601165467;Glucopyranoside, methyl, 2,3-dibenzoate 4-p-toluenesulfonate, alpha-D-;19488-44-9

Chemical Property of Glucopyranoside, methyl, 2,3-dibenzoate 4-p-toluenesulfonate, alpha-D-

Chemical Property:

• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 11
• Exact Mass: 556.14031826
• Heavy Atom Count: 39
• Complexity: 898

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC2C(OC(C(C2OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)OC)CO
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)O[C@@H]2[C@H](O[C@@H]([C@@H]([C@H]2OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)OC)CO

Technology Process of Glucopyranoside, methyl, 2,3-dibenzoate 4-p-toluenesulfonate, alpha-D-

There total 3 articles about Glucopyranoside, methyl, 2,3-dibenzoate 4-p-toluenesulfonate, alpha-D- 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: 96.0%

methyl 2,3-di-O-benzoyl-4-O-(p-tolylsulfonyl)-6-O-trityl-α-D-glucopyranoside (20231-37-2) → methyl 2,3-di-O-benzoyl-4-O-(p-tolylsulfonyl)-α-D-glucopyranoside (19488-44-9)

Guidance literature:

With methanol; boron trifluoride; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)86679-5

Reference yield:

→ methyl 2,3-di-O-benzoyl-4-O-(p-tolylsulfonyl)-α-D-glucopyranoside (19488-44-9)

Guidance literature:

With silver nitrate; acetonitrile; Behandeln des Reaktionsprodukts mit Zink, Eisen und Essigsaeure;

DOI:10.1039/jr9340001177

Reference yield:

methyl 2,3-di-O-benzoyl-α-D-glucopyranoside (4137-35-3,23397-67-3,102518-21-8,109681-62-1,117124-69-3,149035-49-4) → methyl 2,3-di-O-benzoyl-4-O-(p-tolylsulfonyl)-α-D-glucopyranoside (19488-44-9)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / anschliessend Erwaermen mit Toluol-4-sulfonylchlorid

2: aqueous hydrochloric acid; ethanol

With pyridine; hydrogenchloride; ethanol;

DOI:10.1039/jr9530000992 DOI:10.1039/jr9580002511

upstream raw materials:

methyl 2,3-di-O-benzoyl-4-O-(p-tolylsulfonyl)-6-O-trityl-α-D-glucopyranoside

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

Downstream raw materials:

methyl-(O²-acetyl-O⁶-trityl-3,4-anhydro-α-D-galactopyranoside)

methyl 3,4-anhydro-6-O-triphenylmethyl-α-D-galactopyranoside

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

methyl 2,3,6-tri-O-benzoyl-4-O-(p-tolylsulfonyl)-α-D-glucopyranoside

Refernces