The particular sensitivity of silyl ethers of D-glucal toward two Vilsmeier - Haack reagents POCl3·DMF and (CF3SO2)2O·DMF. Their unique and selective conversion to the corresponding C(6)-O-formates

J. P. Lellouche; S. Koeller

doi:10.1021/jo005540t

The particular sensitivity of silyl ethers of D-glucal toward two Vilsmeier - Haack reagents POCl₃·DMF and (CF₃SO₂)₂O·DMF. Their unique and selective conversion to the corresponding C(6)-O-formates

J. P. Lellouche, S. Koeller

Department of Chemistry

Ben-Gurion University of the Negev

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

43 Scopus citations

Abstract

The two electrophilic Vilsmeier - Haack reagents POCl₃·DMF 2 or (CF₃SO₂)₂O·DMF 3 mediate the one-step and selective conversion of O-triethylsilyl (O-TES), O-tert-butyldimethylsilyl (O-TBDMS), O-tert-butyldiphenylsilyl (O-TBDPS), and O-triisopropylsilyl (O-TIPS) ethers of D-glucal to the corresponding C(6)-O-formates.

Original language	English
Pages (from-to)	693-696
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	66
Issue number	3
DOIs	https://doi.org/10.1021/jo005540t
State	Published - 9 Feb 2001

Access to Document

10.1021/jo005540t

Cite this

@article{1e3d0528603d411abf1da2277417af69,

title = "The particular sensitivity of silyl ethers of D-glucal toward two Vilsmeier - Haack reagents POCl3·DMF and (CF3SO2)2O·DMF. Their unique and selective conversion to the corresponding C(6)-O-formates",

abstract = "The two electrophilic Vilsmeier - Haack reagents POCl3·DMF 2 or (CF3SO2)2O·DMF 3 mediate the one-step and selective conversion of O-triethylsilyl (O-TES), O-tert-butyldimethylsilyl (O-TBDMS), O-tert-butyldiphenylsilyl (O-TBDPS), and O-triisopropylsilyl (O-TIPS) ethers of D-glucal to the corresponding C(6)-O-formates.",

author = "Lellouche, {J. P.} and S. Koeller",

year = "2001",

month = feb,

day = "9",

doi = "10.1021/jo005540t",

language = "אנגלית",

volume = "66",

pages = "693--696",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "3",

}

The particular sensitivity of silyl ethers of D-glucal toward two Vilsmeier - Haack reagents POCl₃·DMF and (CF₃SO₂)₂O·DMF. Their unique and selective conversion to the corresponding C(6)-O-formates. / Lellouche, J. P.; Koeller, S.
In: Journal of Organic Chemistry, Vol. 66, No. 3, 09.02.2001, p. 693-696.

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

TY - JOUR

T1 - The particular sensitivity of silyl ethers of D-glucal toward two Vilsmeier - Haack reagents POCl3·DMF and (CF3SO2)2O·DMF. Their unique and selective conversion to the corresponding C(6)-O-formates

AU - Lellouche, J. P.

AU - Koeller, S.

PY - 2001/2/9

Y1 - 2001/2/9

N2 - The two electrophilic Vilsmeier - Haack reagents POCl3·DMF 2 or (CF3SO2)2O·DMF 3 mediate the one-step and selective conversion of O-triethylsilyl (O-TES), O-tert-butyldimethylsilyl (O-TBDMS), O-tert-butyldiphenylsilyl (O-TBDPS), and O-triisopropylsilyl (O-TIPS) ethers of D-glucal to the corresponding C(6)-O-formates.

AB - The two electrophilic Vilsmeier - Haack reagents POCl3·DMF 2 or (CF3SO2)2O·DMF 3 mediate the one-step and selective conversion of O-triethylsilyl (O-TES), O-tert-butyldimethylsilyl (O-TBDMS), O-tert-butyldiphenylsilyl (O-TBDPS), and O-triisopropylsilyl (O-TIPS) ethers of D-glucal to the corresponding C(6)-O-formates.

UR - http://www.scopus.com/inward/record.url?scp=0035830522&partnerID=8YFLogxK

U2 - 10.1021/jo005540t

DO - 10.1021/jo005540t

M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???

C2 - 11430084

AN - SCOPUS:0035830522

SN - 0022-3263

VL - 66

SP - 693

EP - 696

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 3

ER -

The particular sensitivity of silyl ethers of D-glucal toward two Vilsmeier - Haack reagents POCl₃·DMF and (CF₃SO₂)₂O·DMF. Their unique and selective conversion to the corresponding C(6)-O-formates

Abstract

Access to Document

Other files and links

Fingerprint

Cite this