p-nitrophenyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-2,6-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

Base Information

• Chemical Name: p-nitrophenyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-2,6-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• CAS No.: 218617-05-1
• Molecular Formula: C₅₇H₆₅NO₂₄
• Molecular Weight: 1148.14
• Mol file: 218617-05-1.mol

Synonyms:p-nitrophenyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-2,6-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

Chemical Property of p-nitrophenyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-2,6-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-nitrophenyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-2,6-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

There total 9 articles about p-nitrophenyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-2,6-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 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: 65.0%

p-nitrophenyl 2,3,6,2',6'-penta-O-acetyl-β-lactoside (148705-02-6) + o-methoxycarbonylphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranoside (467219-66-5) → p-nitrophenyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-2,6-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (218617-05-1)

Guidance literature:

With N-iodo-succinimide; MS 4 Angstroem; In dichloromethane; at 20 ℃; for 6h;

DOI:10.1016/S0008-6215(02)00093-9

Reference yield: 38.0%

6-O-acetyl-2,3,4-tri-O-benzyl-D-galactopyranosyl fluoride (129785-46-2) + p-nitrophenyl 2,3,6,2',6'-penta-O-acetyl-β-lactoside (148705-02-6) → p-nitrophenyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-2,6-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (218617-05-1)

Guidance literature:

With silver perchlorate; tin(ll) chloride; In dichloromethane;

DOI:10.1016/S0040-4039(98)01897-8

Reference yield:

(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-((2-(methoxycarbonyl)phenyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (382141-78-8) → p-nitrophenyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-2,6-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (218617-05-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 99 percent / NaOMe / methanol / 3 h / 20 °C

2: 85 percent / Et₃N; DMAP / pyridine / 8 h / 20 °C

3: 92 percent / NaH / dimethylformamide / 12 h / 20 °C

4: TBAF / tetrahydrofuran / 12 h / 20 °C

5: pyridine / 7 h

6: 65 percent / MS 4 Angstroem; NIS / CH₂Cl₂ / 6 h / 20 °C

With pyridine; dmap; N-iodo-succinimide; MS 4 Angstroem; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; triethylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(02)00093-9

upstream raw materials:

6-O-acetyl-2,3,4-tri-O-benzyl-D-galactopyranosyl fluoride

p-nitrophenyl 2,3,6,2',6'-penta-O-acetyl-β-lactoside

o-methoxycarbonylphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranoside

2-(methoxycarbonyl)phenyl 1-thio-β-D-galactopyranoside

Downstream raw materials:

(2R,3R,4S,5R,6R)-2-{(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-3-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

p-aminophenyl (α-D-galacopyranosyl)-(1->3)-β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside

p-N-acryloylamidophenyl (α-D-galacopyranosyl)-(1->3)-β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside