Synthesis of a Deoxynojirimycin Analogue from Castanospermine

J.B. Bremner; Brian Skelton; R.J. Smith; G.J. Tarrant; Allan White

doi:10.1016/0040-4039(96)01959-4

Synthesis of a Deoxynojirimycin Analogue from Castanospermine

J.B. Bremner
, Brian Skelton
, R.J. Smith
, G.J. Tarrant
, Allan White

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

8 Citations (Scopus)

Abstract

Ring cleavage of 1,6-O, O-bis-t-butyldimethylsilylcastanospermine 3 with methyl chloroformate followed by deprotection with tetrabutylammonium fluoride gave (1S,6S,7R,8R,8aR)-1-(2'-chloroetbyl)-1,5,6,7,8,8a-hexahydro-6,7, 8,8a-hexahydro-6,7,8-trihydroxy-3H-furo[3,4-a]pyridin-3-one 5. Refluxing 5 with potassium t-butoxide, followed by the addition of NaOH and futher refluxing yielded the deoxynojirimycin analogue (1'S,2R,3R,4R,5S)-2-(1'-hydroxy-2'-propenyl)-piperidine-3,4, 5-triol 2. Copyright (C) 1996 Elsevier Science Ltd

Original language	English
Pages (from-to)	8573-8576
Journal	Tetrahedron Letters
Volume	37
DOIs	https://doi.org/10.1016/0040-4039(96)01959-4
Publication status	Published - 1996

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@article{9b41b422789047849aa00cedc1bf8ce6,

title = "Synthesis of a Deoxynojirimycin Analogue from Castanospermine",

abstract = "Ring cleavage of 1,6-O, O-bis-t-butyldimethylsilylcastanospermine 3 with methyl chloroformate followed by deprotection with tetrabutylammonium fluoride gave (1S,6S,7R,8R,8aR)-1-(2'-chloroetbyl)-1,5,6,7,8,8a-hexahydro-6,7, 8,8a-hexahydro-6,7,8-trihydroxy-3H-furo[3,4-a]pyridin-3-one 5. Refluxing 5 with potassium t-butoxide, followed by the addition of NaOH and futher refluxing yielded the deoxynojirimycin analogue (1'S,2R,3R,4R,5S)-2-(1'-hydroxy-2'-propenyl)-piperidine-3,4, 5-triol 2. Copyright (C) 1996 Elsevier Science Ltd",

author = "J.B. Bremner and Brian Skelton and R.J. Smith and G.J. Tarrant and Allan White",

year = "1996",

doi = "10.1016/0040-4039(96)01959-4",

language = "English",

volume = "37",

pages = "8573--8576",

journal = "Tetrahedron Letters",

publisher = "Elsevier",

}

TY - JOUR

T1 - Synthesis of a Deoxynojirimycin Analogue from Castanospermine

AU - Bremner, J.B.

AU - Skelton, Brian

AU - Smith, R.J.

AU - Tarrant, G.J.

AU - White, Allan

PY - 1996

Y1 - 1996

N2 - Ring cleavage of 1,6-O, O-bis-t-butyldimethylsilylcastanospermine 3 with methyl chloroformate followed by deprotection with tetrabutylammonium fluoride gave (1S,6S,7R,8R,8aR)-1-(2'-chloroetbyl)-1,5,6,7,8,8a-hexahydro-6,7, 8,8a-hexahydro-6,7,8-trihydroxy-3H-furo[3,4-a]pyridin-3-one 5. Refluxing 5 with potassium t-butoxide, followed by the addition of NaOH and futher refluxing yielded the deoxynojirimycin analogue (1'S,2R,3R,4R,5S)-2-(1'-hydroxy-2'-propenyl)-piperidine-3,4, 5-triol 2. Copyright (C) 1996 Elsevier Science Ltd

AB - Ring cleavage of 1,6-O, O-bis-t-butyldimethylsilylcastanospermine 3 with methyl chloroformate followed by deprotection with tetrabutylammonium fluoride gave (1S,6S,7R,8R,8aR)-1-(2'-chloroetbyl)-1,5,6,7,8,8a-hexahydro-6,7, 8,8a-hexahydro-6,7,8-trihydroxy-3H-furo[3,4-a]pyridin-3-one 5. Refluxing 5 with potassium t-butoxide, followed by the addition of NaOH and futher refluxing yielded the deoxynojirimycin analogue (1'S,2R,3R,4R,5S)-2-(1'-hydroxy-2'-propenyl)-piperidine-3,4, 5-triol 2. Copyright (C) 1996 Elsevier Science Ltd

U2 - 10.1016/0040-4039(96)01959-4

DO - 10.1016/0040-4039(96)01959-4

M3 - Article

VL - 37

SP - 8573

EP - 8576

JO - Tetrahedron Letters

JF - Tetrahedron Letters

ER -

Synthesis of a Deoxynojirimycin Analogue from Castanospermine

Abstract

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