Detail of "3978-80-1"

CAS Number:
3978-80-1
Name:
L-Tyrosine,N-[(1,1-dimethylethoxy)carbonyl]-
Superlist Name:
Boc-L-Tyrosine
Molecular Structure:
Formula:
C₁₄H₁₉NO₅
Molecular Weight:
281.31
Synonyms:
Tyrosine,N-carboxy-, N-tert-butyl ester (6CI,7CI);Tyrosine, N-carboxy-, N-tert-butylester, L- (8CI);(2S)-2-[(tert-Butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoic acid;N-(tert-Butoxycarbonyl)tyrosine;N-(tert-Butyloxycarbonyl)-L-tyrosine;N-Boc-L-tyrosine;N-tert-Butoxycarbonyl-L-tyrosine;NSC 334307;tert-Butoxycarbonyl-L-tyrosine;
EINECS:
223-613-7
Density:
1.238 g/cm³
Melting Point:
133-135 °C(lit.)
Boiling Point:
484.9 °C at 760 mmHg
Flash Point:
247.1 °C
Appearance:
white to off-white powder
Hazard Symbols:
Xi
Risk Codes:
36/37/38
Safety:
22-24/25-36-26 Details
particular:
particular

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Reference

Efficient Synthesis of Selectively Protected L-Dopa Derivatives from L-Tyrosine via Reimer-Tiemann and Dakin Reactions: Efficient Synthesis of Selectively Protected L-Dopa Derivatives from L-Tyrosine via Reimer-Tiemann and Dakin Reactions. Jung, Michael E.; Lazarova, Tsvetelina I. (Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095-1569, USA). Journal of Organic Chemistry, 62(5), 1553-1555 (English) 1997 American Chemical Society. CODEN: JOCEAH.Some commonly used reagents like 186689-02-1 and 3978-80-1 are used in this experiment. ISSN: 0022-3263. DOCUMENT TYPE: Journal CA Section: 34 (Amino Acids, Peptides, and Proteins) A new and very efficient (33% overall yield) five-step synthesis of title compd. I (Boc = Me3CO2C) from inexpensive L-tyrosine is described that utilizes a simple formylation (Reimer-Tiemann reaction) and a Dakin reaction as the key steps. Protection of L-tyrosine gave the N-Boc deriv. in 92% yield, which was formylated at the ortho position using a Reimer-Tiemann reaction under the slightly hydrated solid-liq. medium conditions (namely with chloroform and solid sodium hydroxide with a small amt. of water) to give aldehyde II (R = H) in 64% yield based on unrecovered starting material. Benzylation of the phenol gave the benzyl ether aldehyde II (R = CH2Ph) in 71% yield which was converted by the Dakin oxidn. using 30% H2O2 with 4% PhSeSePh as an activator to give the formate 10 which was cleaved directly with methanolic ammonia to afford the desired product I in 78% yield for the two operations. Thus one can convert L-tyrosine into the selectively mono-protected L-Dopa deriv. I in five steps and in 33% overall yield. .

Preparation of (p-hydroxyphenyl)benzylmethylsulfonium chloride (HOBMCl), and reaction with N-protected amino acids: Preparation of (p-hydroxyphenyl)benzylmethylsulfonium chloride (HOBMCl), and reaction with N-protected amino acids. Mukaiyama, Nobuaki; Kouge, Katsushige; Nakatani, Masaru; Okai, Hideo (Sanshin Chem. Ind. Co. Ltd., Hirao 742-11, Japan). Chem. Express, 6(12), 985-8 (English) 1991. CODEN: CHEXEU.Several substances with their cas registry numbers 125662-43-3 and 3978-80-1 may be metioned in this study. ISSN: 0911-9566. DOCUMENT TYPE: Journal CA Section: 34 (Amino Acids, Peptides, and Proteins) Section cross-reference(s): 25 The prepn. of HOBMCl is described; HOBMCl is a reagent for the esterification of N-protected amino acids to give N-protected amino acid benzyl esters. Cysteine was converted to the S-benzyl deriv. because the thiol group is more nucleophilic than the carboxyl group. .

Detail of "3978-80-1"

L-Tyrosine,N-[(1,1-dimethylethoxy)carbonyl]-

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CAS No.3978-80-1 Boc-L-Tyrosine

CAS No.3978-80-1 Boc-L-Tyrosine

CAS No.3978-80-1 Boc-L-Tyrosine

CAS No.3978-80-1 Boc-L-Tyrosine

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CAS No.3978-80-1 Boc-L-Tyrosine

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CAS No.3978-80-1 Boc-L-Tyrosine

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CAS No.3978-80-1 Boc-L-Tyrosine

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CAS No.3978-80-1 Boc-L-Tyrosine

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CAS No.3978-80-1 Boc-L-Tyrosine

Reference