Inter- and intramolecular alcohol additions to exo-glycals

Chuan Fa Chang; Wen Bin Yang; Che Chien Chang; Chun Hung Lin

doi:10.1016/S0040-4039(02)01473-9

Inter- and intramolecular alcohol additions to exo-glycals

Chuan Fa Chang, Wen Bin Yang, Che Chien Chang, Chun Hung Lin

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

27 Citations (Scopus)

Abstract

Various exo-glycals were explored for the glycosidic bond formation and synthesis of spiroacetals in a stereoselective manner. The former reaction was an intermolecular alcohol addition to give the S new stereogenic center, resulting from the nucleophilic attack from the bottom face of the sugar ring. The latter one was carried out by the hydroboration of a sugar diene, followed by a subsequent acid workup.

Original language	English
Pages (from-to)	6515-6519
Number of pages	5
Journal	Tetrahedron Letters
Volume	43
Issue number	37
DOIs	https://doi.org/10.1016/S0040-4039(02)01473-9
Publication status	Published - 2002 Sept 9

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(02)01473-9

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title = "Inter- and intramolecular alcohol additions to exo-glycals",

abstract = "Various exo-glycals were explored for the glycosidic bond formation and synthesis of spiroacetals in a stereoselective manner. The former reaction was an intermolecular alcohol addition to give the S new stereogenic center, resulting from the nucleophilic attack from the bottom face of the sugar ring. The latter one was carried out by the hydroboration of a sugar diene, followed by a subsequent acid workup.",

author = "Chang, {Chuan Fa} and Yang, {Wen Bin} and Chang, {Che Chien} and Lin, {Chun Hung}",

note = "Funding Information: The work is financially supported by National Science Council (NSC-90-2113-M-001-028), National Health Research Institute (NSC-90-2323-B-001-004), and Academia Sinica. We are grateful for the suggestion of one referee about the ring closure based on Baldwin's rule. ",

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T1 - Inter- and intramolecular alcohol additions to exo-glycals

AU - Chang, Chuan Fa

AU - Yang, Wen Bin

AU - Chang, Che Chien

AU - Lin, Chun Hung

N1 - Funding Information: The work is financially supported by National Science Council (NSC-90-2113-M-001-028), National Health Research Institute (NSC-90-2323-B-001-004), and Academia Sinica. We are grateful for the suggestion of one referee about the ring closure based on Baldwin's rule.

PY - 2002/9/9

Y1 - 2002/9/9

N2 - Various exo-glycals were explored for the glycosidic bond formation and synthesis of spiroacetals in a stereoselective manner. The former reaction was an intermolecular alcohol addition to give the S new stereogenic center, resulting from the nucleophilic attack from the bottom face of the sugar ring. The latter one was carried out by the hydroboration of a sugar diene, followed by a subsequent acid workup.

AB - Various exo-glycals were explored for the glycosidic bond formation and synthesis of spiroacetals in a stereoselective manner. The former reaction was an intermolecular alcohol addition to give the S new stereogenic center, resulting from the nucleophilic attack from the bottom face of the sugar ring. The latter one was carried out by the hydroboration of a sugar diene, followed by a subsequent acid workup.

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U2 - 10.1016/S0040-4039(02)01473-9

DO - 10.1016/S0040-4039(02)01473-9

M3 - Article

AN - SCOPUS:0037048491

SN - 0040-4039

VL - 43

SP - 6515

EP - 6519

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 37

ER -

Inter- and intramolecular alcohol additions to exo-glycals

Abstract

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