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

Base Information

• Chemical Name: 4-Nitro-benzoic acid (1S,2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-2-((2S,4S,5R,6S)-4,5-diacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-1-methyl-pent-4-ynyl ester
• CAS No.: 476469-59-7
• Molecular Formula: C₂₉H₄₁NO₁₁Si
• Molecular Weight: 607.73
• Mol file: 476469-59-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about 4-Nitro-benzoic acid (1S,2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-2-((2S,4S,5R,6S)-4,5-diacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-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: 86.0%

3,4-di-O-acetyl-L-fucal (54621-94-2) + (2S,3R,4S)-4-(tert-butyldimethylsiloxy)-hex-5-yn-2,3-diol 2-(para-nitrobenzoate ester) (476469-46-2) → 4-Nitro-benzoic acid (1S,2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-2-((2S,4S,5R,6S)-4,5-diacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-1-methyl-pent-4-ynyl ester (476469-59-7)

Guidance literature:

With camphor-10-sulfonic acid; In toluene; at 20 ℃; for 72h;

DOI:10.1021/ol026886o

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 4-Nitro-benzoic acid (1S,2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-2-((2S,4S,5R,6S)-4,5-diacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-1-methyl-pent-4-ynyl ester (476469-59-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 453 mg / imidazole / CH₂Cl₂ / 16 h / 20 °C

2: 86 percent / camphorsulfonic acid / toluene / 72 h / 20 °C

With 1H-imidazole; camphor-10-sulfonic acid; In dichloromethane; toluene;

DOI:10.1021/ol026886o

Reference yield:

(E)-1-Trimethylsilanyl-hex-4-en-1-yn-3-one → 4-Nitro-benzoic acid (1S,2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-2-((2S,4S,5R,6S)-4,5-diacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-1-methyl-pent-4-ynyl ester (476469-59-7)

Guidance literature:

Multi-step reaction with 5 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: HF*pyridine / tetrahydrofuran / 12 h / 0 °C

3.1: 453 mg / imidazole / CH₂Cl₂ / 16 h / 20 °C

4.1: 86 percent / camphorsulfonic acid / toluene / 72 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; cerium(III) chloride; camphor-10-sulfonic acid; pyridine hydrogenfluoride; In tetrahydrofuran; methanol; dichloromethane; toluene; 1.1: Sharpless epoxidation;

DOI:10.1021/ol026886o

upstream raw materials:

3,4-di-O-acetyl-L-fucal

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

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

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