Benzoic acid (1R,2R,3R)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester

Base Information

Chemical Name:Benzoic acid (1R,2R,3R)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester
CAS No.:332061-62-8
Molecular Formula:C₂₅H₄₂O₄Si₂
Molecular Weight:462.777
Hs Code.:

Synonyms:Benzoic acid (1R,2R,3R)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester

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Chemical Property of Benzoic acid (1R,2R,3R)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester

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Technology Process of Benzoic acid (1R,2R,3R)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester

There total 6 articles about Benzoic acid (1R,2R,3R)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 279684-69-4
(2R,3R,4R)-hex-5-yn-2,3,4-triol 2-benzoate ester

: 332061-62-8
Benzoic acid (1R,2R,3R)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1021/ja994229u

Reference yield:

: 53723-96-9
(2E)-6-(trimethylsilyl)hex-2-en-5-yn-4-one

: 332061-62-8
Benzoic acid (1R,2R,3R)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 91 percent / BH₃-SMe₂; (R)-2-methyl-CBS-oxazaborolidine / tetrahydrofuran / 3.5 h / -45 °C

2: 76 percent / cumene hydroperoxide; Ti(O-i-Pr)4; L-(+)-diisopropyl tartrate / CH₂Cl₂ / 5.5 h / -30 °C

3: 94 percent / Ph₃P; DEAD / diethyl ether / 4 h / 20 °C

4: 92 percent / KCN; MeOH / 11 h

5: 91 percent / Ti(O-i-Pr)4 / benzene / 70 °C

6: 100 percent / imidazole / dimethylformamide / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; methanol; potassium cyanide; L-(+)-diisopropyl tartrate; Cumene hydroperoxide; dimethylsulfide borane complex; triphenylphosphine; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Reduction / 2: Epoxidation / 3: Mitsunobu reaction / 4: debenzoylation / 5: Addition / 6: silylation;
DOI:10.1021/ja994229u

Reference yield:

: 279684-67-2
(3R,4R,5S)-4,5-epoxyhex-1-yn-3-ol

: 332061-62-8
Benzoic acid (1R,2R,3R)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 91 percent / Ti(O-i-Pr)4 / benzene / 70 °C

2: 100 percent / imidazole / dimethylformamide / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; In N,N-dimethyl-formamide; benzene; 1: Addition / 2: silylation;
DOI:10.1021/ja994229u