4-nitrophenyl tri-O-acetyl-β-D-xylopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xyloside

Base Information

• Chemical Name: 4-nitrophenyl tri-O-acetyl-β-D-xylopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xyloside
• CAS No.: 162088-89-3
• Molecular Formula: C₂₆H₃₁NO₁₆
• Molecular Weight: 613.529
• Mol file: 162088-89-3.mol

Synonyms:4-nitrophenyl tri-O-acetyl-β-D-xylopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xyloside

Chemical Property of 4-nitrophenyl tri-O-acetyl-β-D-xylopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xyloside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-nitrophenyl tri-O-acetyl-β-D-xylopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xyloside

There total 8 articles about 4-nitrophenyl tri-O-acetyl-β-D-xylopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xyloside 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%

acetic anhydride (108-24-7) + p-nitrophenyl β-D-xylopyranosyl-(1->4)-β-D-xylopyranoside (6819-07-4) → 4-nitrophenyl tri-O-acetyl-β-D-xylopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xyloside (162088-89-3)

Guidance literature:

With pyridine; Ambient temperature;

DOI:10.1016/0008-6215(95)00214-E

Reference yield: 67.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-((3R,4S,5R,6S)-4,5-diacetoxy-6-bromo-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester → 4-nitrophenyl tri-O-acetyl-β-D-xylopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xyloside (162088-89-3)

Guidance literature:

With 2,6-dimethylpyridine; silver carbonate;

DOI:10.1016/S0008-6215(97)00209-7

Reference yield: 36.0%

α-D-xylopyranosyl fluoride (3945-26-4,4536-02-1,4556-49-4,4556-50-7,16051-71-1,22893-62-5,90822-01-8,108393-17-5) + acetic anhydride (108-24-7) + p-nitrophenyl β-D-xylopyranoside (2001-96-9) → 4-nitrophenyl (2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->3)-O-2,4-di-O-acetyl-β-D-xylopyranoside + 4-nitrophenyl tri-O-acetyl-β-D-xylopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xyloside (162088-89-3) + 4-nitrophenyl O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1<*>4)-O-(2,3-di-O-acetyl-β-D-xylopyranosyl)-(1<*>4)-2,3-di-O-acetyl-β-D-xylopyranoside + 1-O-(4-nitrophenyl)-2,3,4-tri-O-acetyl-β-D-xylopyranoside (24624-78-0,58902-46-8,67006-13-7,94921-62-7,94921-63-8,109526-97-8)

Guidance literature:

α-D-xylopyranosyl fluoride; p-nitrophenyl β-D-xylopyranoside; With Bhxglycosynthase E₃₃₄G mutant; at 20 ℃; for 24h; pH=7; aq. phosphate buffer; Enzymatic reaction;

acetic anhydride; With pyridine; dmap; at 20 ℃; for 16h;

DOI:10.1002/cbic.201100229

upstream raw materials:

2,3,4-tri-O-acetyl-α-D-xylopyranosyl trichloroacetimidate

1-O-(4-nitrophenyl)-2,3-di-O-acetyl-β-D-xylopyranoside

acetic anhydride

p-nitrophenyl β-D-xylopyranosyl-(1->4)-β-D-xylopyranoside

Downstream raw materials:

p-nitrophenyl β-D-xylopyranosyl-(1->4)-β-D-xylopyranoside

Refernces

• 1、 Mechaly, Adva,Belakhov, Valery,Shoham, Yuval,Baasov, Timor. "An efficient chemical-enzymatic synthesis of 4-nitrophenyl β- xylobioside: A chromogenic substrate for xylanases". . p. 111 - 115. Retrieved 2007/10/03.
• 2、 Ziser, Lothar,Withers, Stephen G.. "A short synthesis of β-xylobiosides". . p. 9 - 18. Retrieved 2007/10/02.