A versatile and new highly stereoselective approach to the synthesis of l-glycero-d-manno-heptopyranosides

G. J.P.H. Boons; G. A. van der Marel; J. H. van Boom

doi:10.1016/S0040-4039(00)95167-0

A versatile and new highly stereoselective approach to the synthesis of l-glycero-d-manno-heptopyranosides

G. J.P.H. Boons^*, G. A. van der Marel, J. H. van Boom

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

The reaction of (phenyldimethyl)silylmethylmagnesium chloride with benzyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside affords the corresponding L-glycero-D-manno-addition product having at C-7 the phenyldimethylsilyl (PDMSi) group. The latter silanyl compound survived benzylation as well as glycosylation at OH-6, and the PDMSi group could be unmasked with overall retention of configuration to give a free hydroxyl.

Original language	English
Pages (from-to)	229-232
Number of pages	4
Journal	Tetrahedron Letters
Volume	30
Issue number	2
DOIs	https://doi.org/10.1016/S0040-4039(00)95167-0
Publication status	Published - 1 Jan 1989
Externally published	Yes

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title = "A versatile and new highly stereoselective approach to the synthesis of l-glycero-d-manno-heptopyranosides",

abstract = "The reaction of (phenyldimethyl)silylmethylmagnesium chloride with benzyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside affords the corresponding L-glycero-D-manno-addition product having at C-7 the phenyldimethylsilyl (PDMSi) group. The latter silanyl compound survived benzylation as well as glycosylation at OH-6, and the PDMSi group could be unmasked with overall retention of configuration to give a free hydroxyl.",

author = "Boons, {G. J.P.H.} and {van der Marel}, {G. A.} and {van Boom}, {J. H.}",

year = "1989",

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doi = "10.1016/S0040-4039(00)95167-0",

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T1 - A versatile and new highly stereoselective approach to the synthesis of l-glycero-d-manno-heptopyranosides

AU - Boons, G. J.P.H.

AU - van der Marel, G. A.

AU - van Boom, J. H.

PY - 1989/1/1

Y1 - 1989/1/1

N2 - The reaction of (phenyldimethyl)silylmethylmagnesium chloride with benzyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside affords the corresponding L-glycero-D-manno-addition product having at C-7 the phenyldimethylsilyl (PDMSi) group. The latter silanyl compound survived benzylation as well as glycosylation at OH-6, and the PDMSi group could be unmasked with overall retention of configuration to give a free hydroxyl.

AB - The reaction of (phenyldimethyl)silylmethylmagnesium chloride with benzyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside affords the corresponding L-glycero-D-manno-addition product having at C-7 the phenyldimethylsilyl (PDMSi) group. The latter silanyl compound survived benzylation as well as glycosylation at OH-6, and the PDMSi group could be unmasked with overall retention of configuration to give a free hydroxyl.

UR - http://www.scopus.com/inward/record.url?scp=0000782113&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)95167-0

DO - 10.1016/S0040-4039(00)95167-0

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SN - 0040-4039

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SP - 229

EP - 232

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 2

ER -

A versatile and new highly stereoselective approach to the synthesis of l-glycero-d-manno-heptopyranosides

Abstract

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