REGIOSELECTIVE GLYCOSYLATION OF UNPROTECTED METHYL HEXOPYRANOSIDE BY TRANSIENT MASKING WITH ARYLBORONIC ACID

被引：22

作者：

Nishino, Takashi ^{[1
]}

Ohya, Yohei ^{[1
]}

Murai, Rie ^{[1
]}

Shirahata, Tatsuya ^{[1
]}

Yamamoto, Daisuke ^{[1
]}

Makino, Kazuishi ^{[1
]}

Kaji, Eisuke ^{[1
]}

机构：

[1] Kitasato Univ, Sch Pharm, Minato Ku, Tokyo 1088641, Japan

来源：

HETEROCYCLES | 2012年 / 84卷 / 02期

关键词：

Oligosaccharide; Glycosylation; Regioselectivity; Arylboronic Acid; STANNYLENE ACTIVATION; ATRACTYLODES-LANCEA; GLYCOSIDE SYNTHESIS; GALACTOPYRANOSIDES; OLIGOSACCHARIDES; PROTECTION; RHIZOMES; SUGARS;

D O I：

10.3987/COM-11-S(P)94

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Unprotected methyl alpha/beta-D-galactopyranoside, alpha/beta-D-glucopyranoside, alpha-L-fucopyranoside, and alpha-L-rhamnopyranoside were regioselectively glycosylated by treatment with per-O-pivaloyl-alpha-D-glycopyranosyl bromide to give glycosyl-beta(1 -> 3)-galactopyranoside, glycosyl-beta(1 -> 2/3)-glucopyranoside, glycosyl-beta(1-2)-fucopyranoside, and glycosyl-beta(1 -> 4)-rhamnopyranoside, respectively. The reaction mainly occurred at the secondary hydroxy group, even in the presence of a primary hydroxy group, which was masked with arylboronic acid.

引用

页码：1123 / 1140

页数：18

共 18 条

[1] Regioselective glycosylation of fully unprotected methyl hexopyranosides by means of transient masking of hydroxy groups with arylboronic acids
Kaji, Eisuke
Nishino, Takashi
Ishige, Koji
Ohya, Yohei
Shirai, Yuko
TETRAHEDRON LETTERS, 2010, 51 (12) : 1570 - 1573
[2] Regioselective Glycosylation of Unprotected Phenyl 1-Thioglycopyranosides with Phenylboronic Acid as a Transient Masking Group
Fenger, Thomas Hauch
Madsen, Robert
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (26) : 5923 - 5933
[3] Thermodynamically Controlled Regioselective Glycosylation of Fully Unprotected Sugars through Bis(boronate) Intermediates
Kaji, Eisuke
Yamamoto, Daisuke
Shirai, Yuko
Ishige, Koji
Arai, Yoshika
Shirahata, Tatsuya
Makino, Kazuishi
Nishino, Takashi
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (17) : 3536 - 3539
[4] Stannylene-Mediated Regioselective 6-O-Glycosylation of Unprotected Phenyl 1-Thioglycopyranosides
Maggi, Agnese
Madsen, Robert
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (13) : 2683 - 2691
[5] Halide-mediated regioselective 6-O-glycosylation of unprotected hexopyranosides with perbenzylated glycosyl bromide donors
Niedbal, Dominika Alina
Madsen, Robert
TETRAHEDRON, 2016, 72 (03) : 415 - 419
[6] Regioselective, Tin-Free Sulfation of Unprotected Hexopyranosides by Using Phenylboronic Acid
Fukuhara, Kenji
Shimada, Naoyuki
Nishino, Takashi
Kaji, Eisuke
Makino, Kazuishi
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (05) : 902 - 905
[7] Regio- and stereoselective glycosylation of 2-(o-dihydroxyborylbenzyl) thioglucoside and unprotected methyl glycosides
Lam, Sarah
Hsu, Mei-Yuan
Wang, Cheng-Chung
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2020, 67 (03) : 446 - 450
[8] Highly Regioselective Monoacylation of Unprotected Glucopyranoside Using Transient Directing-Protecting Groups
Rocheleau, Sylvain
Pottel, Joshua
Huskic, Igor
Moitessier, Nicolas
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (03) : 646 - 656
[9] Regioselective glycosylation of unprotected mannosides: A convenient access to high-mannose type saponins
Pakulski, Z
POLISH JOURNAL OF CHEMISTRY, 2005, 79 (02) : 361 - 367
[10] Regioselective conversion of primary alcohols into iodides in unprotected methyl furanosides and pyranosides
Skaanderup, PR
Poulsen, CS
Hyldtoft, L
Jorgensen, MR
Madsen, R
SYNTHESIS-STUTTGART, 2002, (12): : 1721 - 1727

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