Benzoic acid (1R,2R,3S)-2-[(2S,4S,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester

Base Information

Chemical Name:Benzoic acid (1R,2R,3S)-2-[(2S,4S,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester
CAS No.:279684-80-9
Molecular Formula:C₃₇H₆₆O₇Si₃
Molecular Weight:707.183
Hs Code.:

Benzoic acid (1R,2R,3S)-2-[(2S,4S,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester

Synonyms:Benzoic acid (1R,2R,3S)-2-[(2S,4S,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester

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Chemical Property of Benzoic acid (1R,2R,3S)-2-[(2S,4S,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester

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Technology Process of Benzoic acid (1R,2R,3S)-2-[(2S,4S,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester

There total 10 articles about Benzoic acid (1R,2R,3S)-2-[(2S,4S,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-(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: 83.0%

: 279684-76-3
3,4-bis-(tert-butyldimethylsilyl)-1,5-anhydro-2,6-dideoxy-D-ribo-hex-1-enitol

: 279684-79-6
(2R,3R,4S)-4-(tert-butyldimethylsiloxy)-hex-5-yne-2,3-diol 2-benzoate ester

: 279684-80-9
Benzoic acid (1R,2R,3S)-2-[(2S,4S,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester

Guidance literature:: With camphor-10-sulfonic acid; In toluene; at 20 ℃; for 12h;
DOI:10.1021/ja994229u

Reference yield:

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

: 279684-80-9
Benzoic acid (1R,2R,3S)-2-[(2S,4S,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-(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: 100 percent / Ti(O-i-Pr)4 / benzene / 0.5 h / 70 °C

4: 100 percent / Bu₄NF / tetrahydrofuran / 0.5 h / 20 °C

5: 83 percent / imidazole / dimethylformamide / 1 h / 20 °C

6: 83 percent / CSA / toluene / 12 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; L-(+)-diisopropyl tartrate; Cumene hydroperoxide; dimethylsulfide borane complex; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 1: Reduction / 2: Epoxidation / 3: Addition / 4: desilylation / 5: silylation / 6: glycosylation;
DOI:10.1021/ja994229u

Reference yield:

: (R)-1-(trimethylsilyl)hex-4-en-1-yn-3-ol

: 279684-80-9
Benzoic acid (1R,2R,3S)-2-[(2S,4S,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 76 percent / cumene hydroperoxide; Ti(O-i-Pr)4; L-(+)-diisopropyl tartrate / CH₂Cl₂ / 5.5 h / -30 °C

2: 100 percent / Ti(O-i-Pr)4 / benzene / 0.5 h / 70 °C

3: 100 percent / Bu₄NF / tetrahydrofuran / 0.5 h / 20 °C

4: 83 percent / imidazole / dimethylformamide / 1 h / 20 °C

5: 83 percent / CSA / toluene / 12 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; L-(+)-diisopropyl tartrate; Cumene hydroperoxide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 1: Epoxidation / 2: Addition / 3: desilylation / 4: silylation / 5: glycosylation;
DOI:10.1021/ja994229u