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Volumn 22, Issue 36, 1981, Pages 3493-3496

A new synthesis of biotin

Author keywords

[No Author keywords available]

Indexed keywords

BIOTIN;

DRUG ANALYSIS; DRUG IDENTIFICATION; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; PRELIMINARY COMMUNICATION; THEORETICAL STUDY;

EID: 0019481235 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(01)81940-7 Document Type: Article

Times cited : (21)

References (16)

2
- 0018840173
- and refs. cited therein
- (1980) Chem. Ber. , vol.113 , pp. 607
- Fliri¹ Hohenlohe-Oehringen²

3
- 84918348294
- M. Goldberg and L. Sternbach, US-Patent 2 489 232, 2 489 235 and 2 489 238 (1949).

4
- 0343631136
- Studies on Thiophene Compounds. XIX. Syntheses of 2, 3, 4, 5-Tetradehydrobiotin and 2, 3, 4, 5-Tetradehydronorbiotin
- (1962) Bulletin of the Chemical Society of Japan , vol.35 , pp. 432
- Nishimura¹ Emoto²

5
- 0013777454
- Dokl. Akad. Nauk. SSR
- (1965) Dokl. Akad. Nauk. SSR , vol.162 , pp. 120
- Fabrichnyi¹ Shalavina² Goldfarb³

7
- 0342326129
- The Total Synthesis of 2,3,4,5-Tetradehydrobiotin1
- (1945) Journal of the American Chemical Society , vol.67 , pp. 731
- Cheeney¹ Piening²

8
- 0001370296
- (1980) J. Org. Chem. , vol.45 , pp. 617
- Rossy¹ Hoffmann² Müller³

9
- 84918348293
- Benzylidenaminoacetonitrile was condensed with ethylthioformate in a manner analogous to the known procedures (see ref. 6b) used for the preparation of 5-substituted diamino-thiophenes. The resulting sodium salt (E/Z mixture 8: 2) was allowed to react with methyl chloroacetate; cyclization of the intermediate using sodium methylate in methanol afforded 4-N-benzylideneamino-3-amino-2-carboxythiophene. Treatment with hydrogen chloride in wet ether and subsequent neutralization gave 2 in an overall yield of 45 %.

11
- 84981870813
- Einfache Synthese organischer Thionester [1]
- (1963) Zeitschrift für Chemie , vol.3 , pp. 310
- Mayer¹ Berthold²

12
- 84918348292
- 4, yielding a 60: 40 mixture of the 4-nitro- (mp. 113–116°C) and 5-nitroderivative (mp. 176 – 178°C). After the facile separation of these isomers by crystallisation from toluene, 2 was prepared by saponification with sodium methylate in methanol followed by hydrogenation of the nitro group.

13
- 0000178515
- A Convenient Synthesis of 2-Substituted 3-Hydroxy- and 3-Amino-Thiophens from Derivatives of 2-Chloroacrylic Acid
- (1979) Synthetic Communications , vol.9 , pp. 731
- Huddleston¹ Barker²

14
- 84963403358
- Eine Partialsynthese des „all”-trans-Methyl-bixins und des „all”-trans-4.4′-Desdimethyl-methyl-bixins
- (1959) Chemische Berichte , vol.92 , pp. 3111
- Buchta¹ Andree²

15
- 84918364356
- J. Vasilevkis, DOS 2 730 341 (1978). The conditions used in our synthesis are similar to those employed in the above mentioned independent work and are milder than those used in previous attempts to hydrogenate thiophenes; see
- (1978) Adv. in Catalysis , vol.27 , pp. 295

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