REDOX GLYCOSIDATION - THE USE OF NOZAKI-TAKAI METHYLENYLATION IN A HIGHLY STEREOSELECTIVE SYNTHESIS OF SUCROSE

被引：12

作者：

BARRETT, AGM ^{[1
]}

MELCHER, LM ^{[1
]}

BEZUIDENHOUDT, BCB ^{[1
]}

机构：

[1] NORTHWESTERN UNIV,DEPT CHEM,EVANSTON,IL 60208

来源：

CARBOHYDRATE RESEARCH | 1992年 / 232卷 / 02期

关键词：

D O I：

10.1016/0008-6215(92)80059-A

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Sequential reaction of 2,3,4,6-tetra-O-benzyl-D-glucopyranose (7) with butyllithium and 2-[2,3,5-tri-O-benzyl-4-O-(tert-butyldiphenylsilyl)-D-arabinonoyl]thio-3-nitropyridine (6) at -78-degrees gave 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyl 2,3,5-tri-O-benzyl-4-O-(tert-butyldiphenylsilyl)-D-arabinonate (8; 71%, alpha:beta > 50:1). Ester carbonyl methylenylation, desilylation, and iodoetherification in the presence of silica gave 3,4,6-tri-O-benzyl-1-deoxy-1-iodo-(2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyl)-beta-D-fructofuranoside (15; 44%, alpha:beta > 50:1). This neopentylic iodide 15 was converted into sucrose (1; 80%) by free-radical substitution using TEMPO (24) followed by sodium-ammonia reduction, acetylation, and Zemplen methanolysis.

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页码：259 / 272

页数：14

相关论文

共 49 条

[31] AEROBIC CONVERSION OF ORGANIC HALIDES TO ALCOHOLS - AN OXYGENATIVE RADICAL CYCLIZATION [J].

NAKAMURA, E ;

INUBUSHI, T ;

AOKI, S ;

MACHII, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) :8980-8982

[32] SYNTHESIS OF SUCROSE AND OF ALPHA-D-GLUCOPYRANOSYL ALPHA-D-FRUCTOFURANOSIDE THROUGH USE OF 1,3,4,6-TETRA-O-BENZYL-D-FRUCTOFURANOSE [J].

NESS, RK ;

FLETCHER, HG .

CARBOHYDRATE RESEARCH, 1971, 17 (02) :465-&

[33] ALKYLIDENATION OF ESTER CARBONYL GROUPS BY MEANS OF A REAGENT DERIVED FROM RCHBR2, ZN, TICL4, AND TMEDA - STEREOSELECTIVE PREPARATION OF (Z)-ALKENYL ETHERS [J].

OKAZOE, T ;

TAKAI, K ;

OSHIMA, K ;

UTIMOTO, K .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (19) :4410-4412

[34] DEUTERIUM-INDUCED DIFFERENTIAL ISOTOPE SHIFT C-13 NMR .1. RESONANCE RE-ASSIGNMENTS OF MONOSACCHARIDES AND DISACCHARIDES [J].

PFEFFER, PE ;

VALENTINE, KM ;

PARRISH, FW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (05) :1265-1274

[35] STEREOCHEMICAL CONTROL IN ACYLATION OF 2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE A ROUTE TO 1-O-ACYL-ALPHA-AND-BETA-D-GLUCOPYRANOSES [J].

PFEFFER, PE ;

ROTHMAN, ES ;

MOORE, GC .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (17) :2925-2927

[36] TITANIUM-MEDIATED METHYLENE-TRANSFER REACTIONS - DIRECT CONVERSION OF ESTERS INTO VINYL ETHERS [J].

PINE, SH ;

ZAHLER, R ;

EVANS, DA ;

GRUBBS, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (09) :3270-3272

[37] 1-METHYLENE SUGARS AS C-GLYCOSIDE PRECURSORS [J].

RAJANBABU, TV ;

REDDY, GS .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (26) :5458-5461

[38] STEREOSELECTIVITY OF ELECTROPHILE-PROMOTED CYCLIZATIONS OF GAMMA-HYDROXYALKENES - AN INVESTIGATION OF CARBOHYDRATE-DERIVED AND MODEL SUBSTRATES [J].

REITZ, AB ;

NORTEY, SO ;

MARYANOFF, BE ;

LIOTTA, D ;

MONAHAN, R .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (19) :4191-4202

[39] STEREOCONTROLLED SYNTHESIS OF CIS-2,5-DISUBSTITUTED TETRAHYDROFURANS AND CIS-LINALYL AND TRANS-LINALYL OXIDES [J].

RYCHNOVSKY, SD ;

BARTLETT, PA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (13) :3963-3964

[40]

SCHMIDT OT, 1963, METHODS CARBOHYDR CH, V2, P324

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