Use of polymers as protecting groups in organic synthesis. Preparation of partially substituted derivatives of D-glucose

Jean M.J. Fréchet; Geneviève Pellé

doi:10.1039/C39750000225

Use of polymers as protecting groups in organic synthesis. Preparation of partially substituted derivatives of D-glucose

Jean M.J. Fréchet^*, Geneviève Pellé

^*Corresponding author for this work

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

40 Scopus citations

Abstract

Two types of insoluble polystyrene resins bearing vinylbenzaldehyde units have been prepared and used with high efficiency as temporary protecting groups in the synthesis of 2,3 disubstituted derivatives of methyl α-D- glucopyranoside.

Original language	English (US)
Pages (from-to)	225-226
Number of pages	2
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	6
DOIs	https://doi.org/10.1039/C39750000225
State	Published - 1975
Externally published	Yes

Bibliographical note

Funding Information:
Another glucosidic com- ponent of the mixture (9) isolated in 15% yield contained only one benzyl group and could not be crystallized. Similar benzylation of (3)at room temperature with NaH and benzyl chloride in dimethylformamide or KOBu t and benzyl chloride in tetrahydrofuran produced better yields of (8) (30-40%), together with some monobenzylated product (9). The increase in yield observed in the last two benzylations is probably due to the better swelling proper- ties of dimethylformamide and tetrahydrofuran as com-pared to Me,SO. Thus, accessibility of the reactive sites is favoured in the better swelling agents and this results in a more complete benzylation. The fact that a monobenzyl derivative of (3)is obtained in the benzylations may reflect the difficulty of preparing anions on some of the less accessible sites of the resin where ion-ion repulsions may become very important, a fact illustrated by the difficulties experienced3 in the acid-base titrations of resins containing carboxylic acid functional groups. Financial support of the National Research Council of Canada is gratefully acknowledged. (Received, 9th December 1974; Corn. 1481.) 3 JI M. Fr6chet an; C. Schuerch, J. Amer. Chem. SOC.,1971, 93, 492. 4 K. W. Pepper, H. M. Paisley, and M. A. Young, J. Chem. SOC.,1953, 4097. 6D. J. Bell, J. Chem. SOC.,1934, 1177. I? K. Freudenberg and E. Plankenhorn, Bey., 1940, 73, 621.

ASJC Scopus subject areas

Molecular Medicine

Access to Document

10.1039/C39750000225

Cite this

@article{22fd60314ce646828a9aa030f5438cd2,

title = "Use of polymers as protecting groups in organic synthesis. Preparation of partially substituted derivatives of D-glucose",

abstract = "Two types of insoluble polystyrene resins bearing vinylbenzaldehyde units have been prepared and used with high efficiency as temporary protecting groups in the synthesis of 2,3 disubstituted derivatives of methyl α-D- glucopyranoside.",

author = "Fr{\'e}chet, {Jean M.J.} and Genevi{\`e}ve Pell{\'e}",

note = "Funding Information: Another glucosidic com- ponent of the mixture (9) isolated in 15% yield contained only one benzyl group and could not be crystallized. Similar benzylation of (3)at room temperature with NaH and benzyl chloride in dimethylformamide or KOBu t and benzyl chloride in tetrahydrofuran produced better yields of (8) (30-40%), together with some monobenzylated product (9). The increase in yield observed in the last two benzylations is probably due to the better swelling proper- ties of dimethylformamide and tetrahydrofuran as com-pared to Me,SO. Thus, accessibility of the reactive sites is favoured in the better swelling agents and this results in a more complete benzylation. The fact that a monobenzyl derivative of (3)is obtained in the benzylations may reflect the difficulty of preparing anions on some of the less accessible sites of the resin where ion-ion repulsions may become very important, a fact illustrated by the difficulties experienced3 in the acid-base titrations of resins containing carboxylic acid functional groups. Financial support of the National Research Council of Canada is gratefully acknowledged. (Received, 9th December 1974; Corn. 1481.) 3 JI M. Fr6chet an; C. Schuerch, J. Amer. Chem. SOC.,1971, 93, 492. 4 K. W. Pepper, H. M. Paisley, and M. A. Young, J. Chem. SOC.,1953, 4097. 6D. J. Bell, J. Chem. SOC.,1934, 1177. I? K. Freudenberg and E. Plankenhorn, Bey., 1940, 73, 621.",

year = "1975",

doi = "10.1039/C39750000225",

language = "English (US)",

pages = "225--226",

journal = "Journal of the Chemical Society, Chemical Communications",

issn = "0022-4936",

publisher = "Chemical Society",

number = "6",

}

TY - JOUR

T1 - Use of polymers as protecting groups in organic synthesis. Preparation of partially substituted derivatives of D-glucose

AU - Fréchet, Jean M.J.

AU - Pellé, Geneviève

N1 - Funding Information: Another glucosidic com- ponent of the mixture (9) isolated in 15% yield contained only one benzyl group and could not be crystallized. Similar benzylation of (3)at room temperature with NaH and benzyl chloride in dimethylformamide or KOBu t and benzyl chloride in tetrahydrofuran produced better yields of (8) (30-40%), together with some monobenzylated product (9). The increase in yield observed in the last two benzylations is probably due to the better swelling proper- ties of dimethylformamide and tetrahydrofuran as com-pared to Me,SO. Thus, accessibility of the reactive sites is favoured in the better swelling agents and this results in a more complete benzylation. The fact that a monobenzyl derivative of (3)is obtained in the benzylations may reflect the difficulty of preparing anions on some of the less accessible sites of the resin where ion-ion repulsions may become very important, a fact illustrated by the difficulties experienced3 in the acid-base titrations of resins containing carboxylic acid functional groups. Financial support of the National Research Council of Canada is gratefully acknowledged. (Received, 9th December 1974; Corn. 1481.) 3 JI M. Fr6chet an; C. Schuerch, J. Amer. Chem. SOC.,1971, 93, 492. 4 K. W. Pepper, H. M. Paisley, and M. A. Young, J. Chem. SOC.,1953, 4097. 6D. J. Bell, J. Chem. SOC.,1934, 1177. I? K. Freudenberg and E. Plankenhorn, Bey., 1940, 73, 621.

PY - 1975

Y1 - 1975

N2 - Two types of insoluble polystyrene resins bearing vinylbenzaldehyde units have been prepared and used with high efficiency as temporary protecting groups in the synthesis of 2,3 disubstituted derivatives of methyl α-D- glucopyranoside.

AB - Two types of insoluble polystyrene resins bearing vinylbenzaldehyde units have been prepared and used with high efficiency as temporary protecting groups in the synthesis of 2,3 disubstituted derivatives of methyl α-D- glucopyranoside.

UR - http://www.scopus.com/inward/record.url?scp=37049128842&partnerID=8YFLogxK

U2 - 10.1039/C39750000225

DO - 10.1039/C39750000225

M3 - Article

AN - SCOPUS:37049128842

SN - 0022-4936

SP - 225

EP - 226

JO - Journal of the Chemical Society, Chemical Communications

JF - Journal of the Chemical Society, Chemical Communications

IS - 6

ER -

Use of polymers as protecting groups in organic synthesis. Preparation of partially substituted derivatives of D-glucose

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this