21035-77-8Relevant academic research and scientific papers
SYNTHESIS OF A KEY INTERMEDIATE FOR D-BIOTIN VIA 1,3-CYCLOADDITION OF A THIOCARBONYL YLIDE AND SILA PUMMERER REARRANGEMENT
Yamano, Toru,Tanaka, Mitsutaka,Takanohashi, Kunio
, p. 2397 - 2406 (2007/10/02)
An efficient preparation of a d-biotin intermediate, (+/-)-(3aα,4α,6aα)-1,3-dibenzyl-3a,4,6,6a-tetrahydro-4-hydroxy-1H-thienoimidazol-2(3H)-one was accomplished by use of 1,3-cycloaddition of a thiocarbonyl ylide, Curtius rearrangement and sila-Pum
Optical Resolution of a d-Biotin Chiral Intermediate by Use of Lipoprotein Lipase
Tokuyama, Shinji,Yamano, Toru,Aoki, Isao,Takanohashi, Kunio,Nakahama, Kazuo
, p. 741 - 744 (2007/10/02)
An efficient optical resolution of (+/-)-3aα,4α,6aα)-1,3-dibenzyl-3a,4,6,6a-tetrahydro-4-hydroxy-1H-thienoimidazol-2(3H)-one was accomplished by acylation with lipoprotein lipase from Pseudomonas aeruginosa TE3285 in toluene. The lipase acylated (R)-1 enantioselectively, and unreacted (S)-1, which is a chiral d-biotin intermediate, was isolated in excellent chemical and optical yields (>99percent e.e.). Effects of acylating agents, water content and molecular sieves were also investigated.
Synthesis of d-Biotin Chiral Intermediates via a Biochemical Method
Yamano, Toru,Tokuyama, Shinji,Aoki, Isao,Nishiguchi, Yumiko,Nakahama, Kazuo,Takanohashi, Kunio
, p. 1456 - 1460 (2007/10/02)
The enzyme-catalyzed kinetic resolution of (+/-)-(3aα,4α,6aα)-4-acetoxy-1,3-dibenzyl-3a,4,6,6a-tetrahydro-1H-thienoimidazol-2(3H)-one was examined.Lipase B from Pseudomonas fragi and rabbit liver esterase gave (-)--1,3-dibenzyl-3a,4,6,6a-tetrahydro-4-hydroxy-1H-thienoimidazol-2(3H)-one , while Streptomyces rochei var. volubilis gave the alcohol (S)-(2), which is a key intermediate in the synthesis of d-biotin, with high enantioselectivity.
Synthesis of (+)-biotin: Efficient resolution of key intermediates
Bihovsky,Bodepudi
, p. 7667 - 7676 (2007/10/02)
Enantiomerically pure 4-chlorothieno[3,4-d]imidazol-2-one (+)-2 and thieno[3,4-d]imidazol-2,4-dione (+)-5, key intermediates in independent routes to (+)-biotin (6), have been prepared by resolution via the corresponding diastereomeric ethers (3d-g and 3'd-g). Efficient procedures to recycle the undesired diastereomers and recover the chiral auxiliary have been developed.
Nucleophilic Displacements on an α-Chloro Thioether by Organocuprates: A Novel Synthesis of Desoxybiotin
Bates, Hans Aaron,Rosenblum, Stuart B.
, p. 3447 - 3451 (2007/10/02)
Reactions of organometallic reagents with α-chloro thioether 2, which is readily prepared from thienoimidazolone 1, have been investigated as an approach to the synthesis of biotin (10).Methyllithium and methylmagnesium bromide attack exclusively from the less hindered exo face, affording 4, while lithium dimethylcuprate attacks from the endo face with inversion of configuration, affording 5.Lithium dipentylcuprate affords predominantly exo isomer 6, while halide-free lithium methylpentylcuprate affords predominantly endo isomer 7.Debenzylation of 7 yields desoxybiotin (9) which can be microbially oxidized to biotin (10).Alternatively, 2 was hydrolyzed and oxidized to thiolactone 13, a known precursor of biotin.
