4-methoxyphenyl (2,3,4-tri-O-benzyl-α-D-rhamnopyranosyl)-(1→3)-4-O-acetyl-2-O-benzyl-α-L-fucopyranoside

Base Information

Chemical Name:4-methoxyphenyl (2,3,4-tri-O-benzyl-α-D-rhamnopyranosyl)-(1→3)-4-O-acetyl-2-O-benzyl-α-L-fucopyranoside
CAS No.:1628073-56-2
Molecular Formula:C₄₉H₅₄O₁₁
Molecular Weight:818.961
Hs Code.:

Synonyms:4-methoxyphenyl (2,3,4-tri-O-benzyl-α-D-rhamnopyranosyl)-(1→3)-4-O-acetyl-2-O-benzyl-α-L-fucopyranoside

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Chemical Property of 4-methoxyphenyl (2,3,4-tri-O-benzyl-α-D-rhamnopyranosyl)-(1→3)-4-O-acetyl-2-O-benzyl-α-L-fucopyranoside

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Technology Process of 4-methoxyphenyl (2,3,4-tri-O-benzyl-α-D-rhamnopyranosyl)-(1→3)-4-O-acetyl-2-O-benzyl-α-L-fucopyranoside

There total 9 articles about 4-methoxyphenyl (2,3,4-tri-O-benzyl-α-D-rhamnopyranosyl)-(1→3)-4-O-acetyl-2-O-benzyl-α-L-fucopyranoside 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%

: 1163254-38-3
phenyl-2,3,4-tri-O-benzyl-1-thio-β-D-rhamnose

: 1628073-54-0
4-methoxyphenyl 4-O-acetyl-2-O-benzyl-α-L-fucopyranoside

: 1628073-56-2
4-methoxyphenyl (2,3,4-tri-O-benzyl-α-D-rhamnopyranosyl)-(1→3)-4-O-acetyl-2-O-benzyl-α-L-fucopyranoside

Guidance literature:: phenyl-2,3,4-tri-O-benzyl-1-thio-β-D-rhamnose; 4-methoxyphenyl 4-O-acetyl-2-O-benzyl-α-L-fucopyranoside; In dichloromethane; at 20 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -25 ℃; for 1h; stereoselective reaction;
DOI:10.1055/s-0033-1341256

Reference yield:

: 1628073-68-6
C₂₃H₂₈O₆

: 1628073-56-2
4-methoxyphenyl (2,3,4-tri-O-benzyl-α-D-rhamnopyranosyl)-(1→3)-4-O-acetyl-2-O-benzyl-α-L-fucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: water; acetic acid / 1.5 h / 80 °C

2.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 2 h / 20 °C

3.1: water / N,N-dimethyl-formamide / 0.5 h / 20 °C

4.1: dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

4.2: 1 h / -25 °C

With water; toluene-4-sulfonic acid; acetic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1055/s-0033-1341256

Reference yield:

: 7404-35-5,17081-04-8,20853-37-6,27821-10-9,27821-11-0,30021-94-4,33947-15-8,34371-40-9,34371-41-0,35521-79-0,36807-81-5,36807-82-6,50615-78-6,51921-33-6,62182-03-0,64913-16-2,70004-81-8,84622-47-9,87303-56-8,108942-32-1,108942-33-2,109430-94-6,143394-72-3,24332-95-4
1,2,3,4-tetra-O-acetyl-L-fucopyranose

: 1628073-56-2
4-methoxyphenyl (2,3,4-tri-O-benzyl-α-D-rhamnopyranosyl)-(1→3)-4-O-acetyl-2-O-benzyl-α-L-fucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0 - 20 °C / Molecular sieve

2.1: sodium methylate / methanol / 2 h / 20 °C

3.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 6 h / 20 °C

4.1: sodium hydroxide; tetrabutylammomium bromide / N,N-dimethyl-formamide / 5 h / 20 °C

5.1: water; acetic acid / 1.5 h / 80 °C

6.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 2 h / 20 °C

7.1: water / N,N-dimethyl-formamide / 0.5 h / 20 °C

8.1: dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

8.2: 1 h / -25 °C

With trimethylsilyl trifluoromethanesulfonate; tetrabutylammomium bromide; water; sodium methylate; toluene-4-sulfonic acid; acetic acid; sodium hydroxide; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1055/s-0033-1341256