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

Base Information

Chemical Name:4-Nitro-benzoic acid (1S,2R,3S)-2-[(2S,4S,5R,6S)-4-acetoxy-5-((2S,4S,5R,6S)-4,5-diacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester
CAS No.:476469-53-1
Molecular Formula:C₃₇H₅₃NO₁₅Si
Molecular Weight:779.911
Hs Code.:

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

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

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

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

There total 13 articles about 4-Nitro-benzoic acid (1S,2R,3S)-2-[(2S,4S,5R,6S)-4-acetoxy-5-((2S,4S,5R,6S)-4,5-diacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-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: 61.0%

: 477304-82-8
Acetic acid (2S,3R,4S,6S)-3-acetoxy-6-((2S,3R,4S)-4-acetoxy-2-methyl-3,4-dihydro-2H-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-4-yl ester

: 476469-46-2
(2S,3R,4S)-4-(tert-butyldimethylsiloxy)-hex-5-yn-2,3-diol 2-(para-nitrobenzoate ester)

: 476469-53-1
4-Nitro-benzoic acid (1S,2R,3S)-2-[(2S,4S,5R,6S)-4-acetoxy-5-((2S,4S,5R,6S)-4,5-diacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester

Guidance literature:: With hydrogen bromide; triphenylphosphine; In dichloromethane; at 20 ℃; for 9h;
DOI:10.1021/ol026886o

Reference yield:

: 279684-66-1
(3S,4R,5S)-1-(trimethylsilyl)-4,5-epoxyhex-1-yn-3-ol

: 476469-53-1
4-Nitro-benzoic acid (1S,2R,3S)-2-[(2S,4S,5R,6S)-4-acetoxy-5-((2S,4S,5R,6S)-4,5-diacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 95 percent / DIBAL / CH₂Cl₂ / -78 °C

2.1: 92 percent / Et₃N / W(CO)6 / tetrahydrofuran / 5 h / 65 °C / Irradiation

3.1: 95 percent / camphorsulfonic acid / toluene / 5 h / 20 °C

4.1: 83 percent / DIBAL / CH₂Cl₂ / -78 °C

5.1: 87 percent / Et₃N / W(CO)6 / tetrahydrofuran / 65 °C / Irradiation

6.1: Bu₄NF; acetic acid / tetrahydrofuran / 32 h / 0 - 20 °C

6.2: 46 percent / DMAP; Et₃N / tetrahydrofuran / 10 h / 20 °C

7.1: 61 percent / PPh₃; HBr / CH₂Cl₂ / 9 h / 20 °C

With camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen bromide; diisobutylaluminium hydride; acetic acid; triethylamine; triphenylphosphine; tungsten hexacarbonyl; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/ol026886o

Reference yield:

: (E)-1-Trimethylsilanyl-hex-4-en-1-yn-3-one

: 476469-53-1
4-Nitro-benzoic acid (1S,2R,3S)-2-[(2S,4S,5R,6S)-4-acetoxy-5-((2S,4S,5R,6S)-4,5-diacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: NaBH₄; CeCl₃ / CH₂Cl₂; methanol / -78 °C

1.2: 42 percent / L-(+)-DIPT; t-BuOOH / Ti(O-i-Pr)4 / CH₂Cl₂; decane / 5.5 h / -25 °C

2.1: 95 percent / DIBAL / CH₂Cl₂ / -78 °C

3.1: 92 percent / Et₃N / W(CO)6 / tetrahydrofuran / 5 h / 65 °C / Irradiation

4.1: 95 percent / camphorsulfonic acid / toluene / 5 h / 20 °C

5.1: 83 percent / DIBAL / CH₂Cl₂ / -78 °C

6.1: 87 percent / Et₃N / W(CO)6 / tetrahydrofuran / 65 °C / Irradiation

7.1: Bu₄NF; acetic acid / tetrahydrofuran / 32 h / 0 - 20 °C

7.2: 46 percent / DMAP; Et₃N / tetrahydrofuran / 10 h / 20 °C

8.1: 61 percent / PPh₃; HBr / CH₂Cl₂ / 9 h / 20 °C

With sodium tetrahydroborate; cerium(III) chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen bromide; diisobutylaluminium hydride; acetic acid; triethylamine; triphenylphosphine; tungsten hexacarbonyl; In tetrahydrofuran; methanol; dichloromethane; toluene; 1.1: Sharpless epoxidation;
DOI:10.1021/ol026886o