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e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Stereospecific total synthesis of d-biotin from L (+)-cysteine

PN Confalone, G Pizzolato, EG Baggiolini…

Index: Journal of the American Chemical Society, , vol. 99, p. 7020 - 7026

Full Text: HTML

Citation Number: 77

Abstract

... The chemistry of the derived amino bromide 22 is elucidated and involves a further rearrangement implicating the aziridine 23. ... Debenzylation was Journal of the American Chemical Society / 99:21 1 October 12, 1977 Page 4. 1023 ...

 Related Synthetic Route
3-bromo-hexahydro-thieno[3,2-b]pyridin-5-one Structure

59999-70-1

3-bromo-hexahyd...

~%

D-Biotin Structure

58-85-5

D-Biotin

(3aS)-3t-azido-(3ar,7ac)-hexahydro-thieno[3,2-b]pyridin-5-one Structure

57671-73-5

(3aS)-3t-azido-...

~%

D-Biotin Structure

58-85-5

D-Biotin

3-((2S)-4c-amino-3t-bromo-tetrahydro-thiophen-2r-yl)-propionic acid methyl ester, hydrobromide Structure

57671-70-2

3-((2S)-4c-amin...

~%

D-Biotin Structure

58-85-5

D-Biotin

2-[3-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]propyl]propanedioic acid Structure

57671-79-1

2-[3-[(3aS,4S,6...

~%

D-Biotin Structure

58-85-5

D-Biotin

(3aS)-3t-amino-(3ar,7ac)-hexahydro-thieno[3,2-b]pyridin-5-one Structure

57671-75-7

(3aS)-3t-amino-...

~%

D-Biotin Structure

58-85-5

D-Biotin

(3aS)-4t-(3-hydroxy-propyl)-(3ar,6ac)-tetrahydro-thieno[3,4-d]imidazol-2-one Structure

57671-77-9

(3aS)-4t-(3-hyd...

~%

D-Biotin Structure

58-85-5

D-Biotin

Bisnorbiotin Structure

16968-98-2

Bisnorbiotin

~%

D-Biotin Structure

58-85-5

D-Biotin

3-((3aS)-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl)-propionic acid methyl ester Structure

57671-76-8

3-((3aS)-2-oxo-...

~%

D-Biotin Structure

58-85-5

D-Biotin

2-oxo-(3ar,8ac,8bc)-decahydro-thieno[1',2':1,2]thieno[3,4-d]imidazolium, bromide Structure

57671-78-0

2-oxo-(3ar,8ac,...

~%

D-Biotin Structure

58-85-5

D-Biotin

3-bromo-hexahydro-thieno[3,2-b]pyridin-5-one Structure

59999-70-1

3-bromo-hexahyd...

~%

2-[3-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]propyl]propanedioic acid Structure

57671-79-1

2-[3-[(3aS,4S,6...

(3aS)-3t-azido-(3ar,7ac)-hexahydro-thieno[3,2-b]pyridin-5-one Structure

57671-73-5

(3aS)-3t-azido-...

~%

2-[3-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]propyl]propanedioic acid Structure

57671-79-1

2-[3-[(3aS,4S,6...

3-((2S)-4c-amino-3t-bromo-tetrahydro-thiophen-2r-yl)-propionic acid methyl ester, hydrobromide Structure

57671-70-2

3-((2S)-4c-amin...

~%

2-[3-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]propyl]propanedioic acid Structure

57671-79-1

2-[3-[(3aS,4S,6...

(3aS)-3t-amino-(3ar,7ac)-hexahydro-thieno[3,2-b]pyridin-5-one Structure

57671-75-7

(3aS)-3t-amino-...

~%

2-[3-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]propyl]propanedioic acid Structure

57671-79-1

2-[3-[(3aS,4S,6...

(3aS)-4t-(3-hydroxy-propyl)-(3ar,6ac)-tetrahydro-thieno[3,4-d]imidazol-2-one Structure

57671-77-9

(3aS)-4t-(3-hyd...

~%

2-[3-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]propyl]propanedioic acid Structure

57671-79-1

2-[3-[(3aS,4S,6...

Bisnorbiotin Structure

16968-98-2

Bisnorbiotin

~%

2-[3-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]propyl]propanedioic acid Structure

57671-79-1

2-[3-[(3aS,4S,6...

3-((3aS)-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl)-propionic acid methyl ester Structure

57671-76-8

3-((3aS)-2-oxo-...

~%

2-[3-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]propyl]propanedioic acid Structure

57671-79-1

2-[3-[(3aS,4S,6...

2-oxo-(3ar,8ac,8bc)-decahydro-thieno[1',2':1,2]thieno[3,4-d]imidazolium, bromide Structure

57671-78-0

2-oxo-(3ar,8ac,...

Diethyl malonate Structure

105-53-3

Diethyl malonate

~%

2-[3-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]propyl]propanedioic acid Structure

57671-79-1

2-[3-[(3aS,4S,6...

Related Articles: More...
Synthesis of d-biotin from L-cystine via intramolecular [3+ ...

[Baggiolini, Enrico G.; Lee, Hsi Lin; Pizzolato, Giacomo; Uskokovic, Milan R. Journal of the American Chemical Society, 1982 , vol. 104, # 23 p. 6460 - 6462]
Intermolecular and intramolecular α-amidoalkylation reaction...

[Chavan, Subhash P.; Chittiboyina, Amar G.; Ravindranathan; Kamat, Subhash K.; Kalkote, Uttam R. Journal of Organic Chemistry, 2005 , vol. 70, # 5 p. 1901 - 1903]
Synthetic studies on d-biotin, Part 9. An improved asymmetri...

[Chemical and Pharmaceutical Bulletin, , vol. 53, # 7 p. 743 - 746]
Synthesis of d-biotin via dehydrobiotin

[Journal of the American Chemical Society, , vol. 100, # 23 p. 7423 - 7424]
Synthesis of d-biotin via dehydrobiotin

[Journal of the American Chemical Society, , vol. 100, # 23 p. 7423 - 7424]

Detail Synthetic Route


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