4-Methoxyphenyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-benzyl-alpha-L-allopyranosyl)-alpha-L-gulopyranoside

Base Information

• Chemical Name: 4-Methoxyphenyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-benzyl-alpha-L-allopyranosyl)-alpha-L-gulopyranoside
• CAS No.: 717132-49-5
• Molecular Formula: C61H64 O12
• Molecular Weight: 989.172
• DSSTox Substance ID: DTXSID70693680
• Wikidata: Q82622690
• Mol file: 717132-49-5.mol

Synonyms:LacMP 3'-OH, per OBn;DTXSID70693680;M1727;4-Methoxyphenyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-benzyl-alpha-L-allopyranosyl)-alpha-L-gulopyranoside

Chemical Property of 4-Methoxyphenyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-benzyl-alpha-L-allopyranosyl)-alpha-L-gulopyranoside

Chemical Property:

• Refractive Index: 1.637
• PSA: 121.76000
• Density: 1.271g/cm³
• LogP: 10.04510
• XLogP3: 9.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 25
• Exact Mass: 988.43977747
• Heavy Atom Count: 73
• Complexity: 1450

Purity/Quality:

97% ^*data from raw suppliers

Gal[246Bn]β(1-4)Glc[236Bn]-β-MP >95.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)OC2C(C(C(C(O2)COCC3=CC=CC=C3)OC4C(C(C(C(O4)COCC5=CC=CC=C5)OCC6=CC=CC=C6)O)OCC7=CC=CC=C7)OCC8=CC=CC=C8)OCC9=CC=CC=C9
• Isomeric SMILES: COC1=CC=C(C=C1)O[C@H]2[C@H]([C@H]([C@@H]([C@@H](O2)COCC3=CC=CC=C3)O[C@H]4[C@H]([C@H]([C@H]([C@@H](O4)COCC5=CC=CC=C5)OCC6=CC=CC=C6)O)OCC7=CC=CC=C7)OCC8=CC=CC=C8)OCC9=CC=CC=C9

Technology Process of 4-Methoxyphenyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-benzyl-alpha-L-allopyranosyl)-alpha-L-gulopyranoside

There total 8 articles about 4-Methoxyphenyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-benzyl-alpha-L-allopyranosyl)-alpha-L-gulopyranoside 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: 89.0%

4-methoxyphenyl 2,4,6-tri-O-benzyl-3-O-(2-naphthyl)methyl-β-D-galactopyranosyl(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (717132-48-4) → 4-methoxyphenyl 2,4,6-tri-O-benzyl-β-D-galactopyranosyl(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (717132-49-5)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; at 20 ℃; for 1h;

DOI:10.1081/CAR-120037571

Reference yield: 87.0%

4-methoxyphenyl 3-O-allyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (717132-47-3) → 4-methoxyphenyl 2,4,6-tri-O-benzyl-β-D-galactopyranosyl(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (717132-49-5)

Guidance literature:

With toluene-4-sulfonic acid; palladium on activated charcoal; In ethanol; ethyl acetate; at 80 ℃; for 2h;

DOI:10.1081/CAR-120037571

Reference yield:

4-methoxyphenyl (β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside (150412-80-9) → 4-methoxyphenyl 2,4,6-tri-O-benzyl-β-D-galactopyranosyl(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (717132-49-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 66 percent / p-toluenesulfonic acid / dimethylformamide / 4 h / 80 °C

2.1: NaH / dimethylformamide / 2 h / 0 °C

3.1: 13 g / aq. HCl / methanol / 2 h / 50 °C

4.1: Bu₂SnO / methanol / 2 h / Heating

4.2: 88 percent / dimethylformamide / 48 h / 20 °C

5.1: NaH / dimethylformamide / 0.5 h / 0 °C

5.2: 91 percent / dimethylformamide / 1 h / 0 °C

6.1: 87 percent / p-TsOH / Pd/C / ethyl acetate; ethanol / 2 h / 80 °C

With hydrogenchloride; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; ethanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1081/CAR-120037571

upstream raw materials:

4-methoxyphenyl 3-O-allyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

4-methoxyphenyl 2,4,6-tri-O-benzyl-3-O-(2-naphthyl)methyl-β-D-galactopyranosyl(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

4-methoxyphenyl (β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside

4-methoxyphenyl 3,4-O-isopropylidene-β-D-galactopyranosyl(1->4)-β-D-glucopyranoside

Downstream raw materials:

4-methoxyphenyl 2,4,6-tri-O-benzyl-β-D-xylo-hex-3-ulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

4-methoxyphenyl 2,4,6-tri-O-benzyl-3-C-ethoxysulfonylmethyl-β-D-gulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

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