First synthesis of the phosphono analogue of N-acetyl-α-D-mannosamine 1-phosphate

Laura Cipolla; Luigi Lay; Francesco Nicotra; Luigi Panza; Giovanni Russo

doi:10.1039/C39950001993

First synthesis of the phosphono analogue of N-acetyl-α-D-mannosamine 1-phosphate

Laura Cipolla, Luigi Lay, Francesco Nicotra, Luigi Panza, Giovanni Russo

Risultato della ricerca: Contributo su rivista › Articolo in rivista › peer review

Abstract

Reaction of 2,3,5-tri-O-benzyl-D-arabinose with divinylzinc, and subsequent mercuriocyclisation and iododemercuriation stereoselectivity affords the α-C-glucopyranosyl iodide 3 with a free hydroxy group at C-2; temporary protection of the free hydroxy group, treatment of the iodide with triethylphosphite to afford the corresponding phosphonate, deprotection of the hydroxy group, oxidation, oximation, catalytic hydrogenation and acetylation, afford the phosphono analogue of N-acetyl-α-D-mannosamine 1-phosphate.

Lingua originale	Inglese
pagine (da-a)	1993-1994
Numero di pagine	2
Rivista	Chemical Communications
Numero di pubblicazione	19
DOI	https://doi.org/10.1039/C39950001993
Stato di pubblicazione	Pubblicato - 1995
Pubblicato esternamente	Sì

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10.1039/C39950001993

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title = "First synthesis of the phosphono analogue of N-acetyl-α-D-mannosamine 1-phosphate",

abstract = "Reaction of 2,3,5-tri-O-benzyl-D-arabinose with divinylzinc, and subsequent mercuriocyclisation and iododemercuriation stereoselectivity affords the α-C-glucopyranosyl iodide 3 with a free hydroxy group at C-2; temporary protection of the free hydroxy group, treatment of the iodide with triethylphosphite to afford the corresponding phosphonate, deprotection of the hydroxy group, oxidation, oximation, catalytic hydrogenation and acetylation, afford the phosphono analogue of N-acetyl-α-D-mannosamine 1-phosphate.",

author = "Laura Cipolla and Luigi Lay and Francesco Nicotra and Luigi Panza and Giovanni Russo",

year = "1995",

doi = "10.1039/C39950001993",

language = "English",

pages = "1993--1994",

journal = "Chemical Communications",

issn = "0022-4936",

publisher = "Royal Society of Chemistry",

number = "19",

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T1 - First synthesis of the phosphono analogue of N-acetyl-α-D-mannosamine 1-phosphate

AU - Cipolla, Laura

AU - Lay, Luigi

AU - Nicotra, Francesco

AU - Panza, Luigi

AU - Russo, Giovanni

PY - 1995

Y1 - 1995

N2 - Reaction of 2,3,5-tri-O-benzyl-D-arabinose with divinylzinc, and subsequent mercuriocyclisation and iododemercuriation stereoselectivity affords the α-C-glucopyranosyl iodide 3 with a free hydroxy group at C-2; temporary protection of the free hydroxy group, treatment of the iodide with triethylphosphite to afford the corresponding phosphonate, deprotection of the hydroxy group, oxidation, oximation, catalytic hydrogenation and acetylation, afford the phosphono analogue of N-acetyl-α-D-mannosamine 1-phosphate.

AB - Reaction of 2,3,5-tri-O-benzyl-D-arabinose with divinylzinc, and subsequent mercuriocyclisation and iododemercuriation stereoselectivity affords the α-C-glucopyranosyl iodide 3 with a free hydroxy group at C-2; temporary protection of the free hydroxy group, treatment of the iodide with triethylphosphite to afford the corresponding phosphonate, deprotection of the hydroxy group, oxidation, oximation, catalytic hydrogenation and acetylation, afford the phosphono analogue of N-acetyl-α-D-mannosamine 1-phosphate.

UR - http://www.scopus.com/inward/record.url?scp=33745689616&partnerID=8YFLogxK

U2 - 10.1039/C39950001993

DO - 10.1039/C39950001993

M3 - Article

SN - 0022-4936

SP - 1993

EP - 1994

JO - Chemical Communications

JF - Chemical Communications

IS - 19

ER -

First synthesis of the phosphono analogue of N-acetyl-α-D-mannosamine 1-phosphate

Abstract

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