e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Carbohydrate research

Total synthesis of syringalide B, a phenylpropanoid glycoside

Q Li, SC Li, H Li, MS Cai, ZJ Li

Index: Li, Qing; Li, Shu-Chun; Li, Hui; Cai, Meng-Shen; Li, Zhong-Jun Carbohydrate Research, 2005 , vol. 340, # 9 p. 1601 - 1604

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Citation Number: 18

Abstract

The first total synthesis of syringalide B, 2-(4-hydroxyphenyl) ethyl 4-O-[(E)-feruloyl]-β-d- glucopyranoside, is described. The hydroxyl groups were protected with allyloxycarbonyl (Aoc) and allyl groups, which successfully prevent the migration of the feruloyl group during the deblocking procedure.

2-(4-allyloxyphenyl)ethyl 2,3-di-O-allyl-4-O-[(E)-(4-O-allyl)feruloyl]-6-O-allyloxycarbonyl-β-D-glucopyranoside Structure

2-(4-allyloxyph...

~81%

[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate Structure

[(2R,3S,4R,5R,6...

2-(4-allyloxyphenyl)ethyl 2,3-di-O-allyl-β-D-glucopyranoside Structure

2-(4-allyloxyph...

~%

[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate Structure

[(2R,3S,4R,5R,6...

2-(4-allyloxyphenyl)ethyl 2,3-di-O-allyl-4,6-O-benzylidene-β-D-glucopyranoside Structure

2-(4-allyloxyph...

~%

[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate Structure

[(2R,3S,4R,5R,6...

2-(4-allyloxyphenyl)ethyl 2,3-di-O-allyl-6-O-allyloxycarbonyl-β-D-glucopyranoside Structure

2-(4-allyloxyph...

~%

[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate Structure

[(2R,3S,4R,5R,6...

Total synthesis of phenylpropanoid glycosides, grayanoside A...

[Das, Saibal Kumar; Reddy, K. Anantha; Mukkanti Carbohydrate Research, 2007 , vol. 342, # 15 p. 2309 - 2315]

Total synthesis of phenylpropanoid glycosides, grayanoside A...

[Das, Saibal Kumar; Reddy, K. Anantha; Mukkanti Carbohydrate Research, 2007 , vol. 342, # 15 p. 2309 - 2315]

Total synthesis of phenylpropanoid glycosides, grayanoside A...

[Das, Saibal Kumar; Reddy, K. Anantha; Mukkanti Carbohydrate Research, 2007 , vol. 342, # 15 p. 2309 - 2315]

Total synthesis of phenylpropanoid glycosides, grayanoside A...

[Das, Saibal Kumar; Reddy, K. Anantha; Mukkanti Carbohydrate Research, 2007 , vol. 342, # 15 p. 2309 - 2315]

Total synthesis of phenylpropanoid glycosides, grayanoside A...

[Das, Saibal Kumar; Reddy, K. Anantha; Mukkanti Carbohydrate Research, 2007 , vol. 342, # 15 p. 2309 - 2315]