phenyl 3-O-[4-O-(p-methoxybenzyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-1-thio-β-D-xylopyranoside

Base Information

• Chemical Name: phenyl 3-O-[4-O-(p-methoxybenzyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-1-thio-β-D-xylopyranoside
• CAS No.: 261374-44-1
• Molecular Formula: C₂₉H₄₀O₉S
• Molecular Weight: 564.697

Synonyms:phenyl 3-O-[4-O-(p-methoxybenzyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-1-thio-β-D-xylopyranoside

Chemical Property of phenyl 3-O-[4-O-(p-methoxybenzyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-1-thio-β-D-xylopyranoside

Chemical Property:

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Technology Process of phenyl 3-O-[4-O-(p-methoxybenzyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-1-thio-β-D-xylopyranoside

There total 1 articles about phenyl 3-O-[4-O-(p-methoxybenzyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-1-thio-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:

phenyl 3-O-[4-O-(tert-butyldimethylsilyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-1-thio-β-D-xylopyranoside (170451-44-2) → phenyl 3-O-[4-O-(p-methoxybenzyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-1-thio-β-D-xylopyranoside (261374-44-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / TBAF / tetrahydrofuran / 48 h

2: 96 percent / NaI; NaH / tetrahydrofuran / 0.5 h / 65 °C

With tetrabutyl ammonium fluoride; sodium hydride; sodium iodide; In tetrahydrofuran; 1: desilylation / 2: benzylation;

DOI:10.1021/ja993487o

Reference yield: 36.0%

(1S,4R,5R,7R,9R,13S,14R,15S)-4,15-dihydroxy-3,11-dioxo-9-[(E)-2-iodoethenyl]-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.14,7]octadecane (215120-26-6) + phenyl 3-O-[4-O-(p-methoxybenzyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-1-thio-β-D-xylopyranoside (261374-44-1) → (1S,4R,5R,7R,9R,13S,14S,15S)-4-hydroxy-9-[(E)-2-iodovinyl]-15-[[3-O-[4-O-(p-methoxybenzyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-β-D-xylopyranosyl]oxy]-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.14,7]octadecane-3,11-dione (223693-28-5) + (1S,4R,5R,7R,9R,13S,14S,15S)-4-hydroxy-9-[(E)-2-iodovinyl]-15-[[3-O-[4-O-(p-methoxybenzyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-α-D-xylopyranosyl]oxy]-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.14,7]octadecane-3,11-dione

Guidance literature:

With N-Bromosuccinimide; In acetonitrile;

DOI:10.1021/ja993487o

upstream raw materials:

phenyl 3-O-[4-O-(tert-butyldimethylsilyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-1-thio-β-D-xylopyranoside

Downstream raw materials:

(1S,4R,5R,7R,9R,13S,14S,15S)-4-hydroxy-9-[(E)-2-iodovinyl]-15-[[3-O-[4-O-(p-methoxybenzyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-β-D-xylopyranosyl]oxy]-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.1^4,7]octadecane-3,11-dione

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