p-Methoxyphenyl (methyl 4-deoxy-β-L-threo-hex-4-enopyranosyluronate)-(1->2)-[3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-β-D-xylopyranosyl]-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside

Base Information

• Chemical Name: p-Methoxyphenyl (methyl 4-deoxy-β-L-threo-hex-4-enopyranosyluronate)-(1->2)-[3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-β-D-xylopyranosyl]-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside
• CAS No.: 346435-23-2
• Molecular Formula: C₄₄H₅₀O₁₉
• Molecular Weight: 882.87

Synonyms:p-Methoxyphenyl (methyl 4-deoxy-β-L-threo-hex-4-enopyranosyluronate)-(1->2)-[3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-β-D-xylopyranosyl]-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside

Chemical Property of p-Methoxyphenyl (methyl 4-deoxy-β-L-threo-hex-4-enopyranosyluronate)-(1->2)-[3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-β-D-xylopyranosyl]-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside

Chemical Property:

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Technology Process of p-Methoxyphenyl (methyl 4-deoxy-β-L-threo-hex-4-enopyranosyluronate)-(1->2)-[3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-β-D-xylopyranosyl]-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside

There total 18 articles about p-Methoxyphenyl (methyl 4-deoxy-β-L-threo-hex-4-enopyranosyluronate)-(1->2)-[3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-β-D-xylopyranosyl]-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside 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: 72.0%

p-Methoxyphenyl (methyl 4-O-methylsulfonyl-α-D-glucopyranosyluronate)-(1->2)-[3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-β-D-xylopyranosyl]-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside → p-Methoxyphenyl (methyl 4-deoxy-β-L-threo-hex-4-enopyranosyluronate)-(1->2)-[3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-β-D-xylopyranosyl]-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside (346435-23-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 40h;

DOI:10.1039/b009670a

Reference yield:

ethyl 1-thio-β-D-xylopyranoside (2595-46-2) → p-Methoxyphenyl (methyl 4-deoxy-β-L-threo-hex-4-enopyranosyluronate)-(1->2)-[3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-β-D-xylopyranosyl]-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside (346435-23-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 59 percent / CSA / methanol / 2 h / Heating

2: 92 percent / pyridine / CH₂Cl₂ / 3 h / 20 °C

3: 83 percent / molecular sieves 4 Angstroem; NIS; triflic acid / CH₂Cl₂ / 1 h / 0 °C

4: 71 percent / hydrazine acetate / methanol

5: 80 percent / dimethyl(methylthio)sulfonium triflate; molecular sieves 4 Angstroem / diethyl ether / 6 h / 0 °C

6: 87 percent / H₂; aq. AcOH / Pd(OH)2/C / ethyl acetate; methanol / 40 h / 5171.62 Torr

7: 72 percent / DBU / CH₂Cl₂ / 40 h / 20 °C

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen; hydrazinium monoacetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; palladium dihydroxide; In methanol; diethyl ether; dichloromethane; ethyl acetate;

DOI:10.1039/b009670a

Reference yield:

p-Methoxyphenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside (13299-05-3) → p-Methoxyphenyl (methyl 4-deoxy-β-L-threo-hex-4-enopyranosyluronate)-(1->2)-[3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-β-D-xylopyranosyl]-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside (346435-23-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: NaOMe / methanol / 20 °C

2.1: dibutyltin oxide / toluene / Heating

2.2: 5.3 g / toluene / 4 h / -40 - 20 °C

3.1: pyridine / CH₂Cl₂ / 20 °C

4.1: 203 mg / hydrazine acetate / methanol / 6 h / 20 °C

5.1: 83 percent / molecular sieves 4 Angstroem; NIS; triflic acid / CH₂Cl₂ / 1 h / 0 °C

6.1: 71 percent / hydrazine acetate / methanol

7.1: 80 percent / dimethyl(methylthio)sulfonium triflate; molecular sieves 4 Angstroem / diethyl ether / 6 h / 0 °C

8.1: 87 percent / H₂; aq. AcOH / Pd(OH)2/C / ethyl acetate; methanol / 40 h / 5171.62 Torr

9.1: 72 percent / DBU / CH₂Cl₂ / 40 h / 20 °C

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; hydrogen; sodium methylate; hydrazinium monoacetate; di(n-butyl)tin oxide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; palladium dihydroxide; In methanol; diethyl ether; dichloromethane; ethyl acetate; toluene;

DOI:10.1039/b009670a

upstream raw materials:

ethyl 1-thio-β-D-xylopyranoside

p-Methoxyphenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside

p-Methoxyphenyl β-D-xylopyranoside

ethyl 2,3-di-O-benzyl-1-thio-β-D-glucopyranoside

Downstream raw materials:

p-Methoxyphenyl (methyl 2,3-di-O-acetyl-4-deoxy-β-L-threo-hex-4-enopyranosyluronate)-(1->2)-(3,4-di-O-acetyl-β-D-xylopyranosyl)-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside

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